(S)-1-Phenylpropan-2-amine (Dextroamphetamine; (S)-Amphetamine) by Asch

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Reactions (97)

Yield

Substances (1)

Citations (49)

Conditions

References A

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Rx-ID: 44467210 Find similar reactions

B: 78 %Chromat.

With transaminase TA-P1-A06 in aq. phosphate buffer; dimethyl sulfoxide

T=30°C; pH=7.5; 48 h; Enzymatic reaction;

Martínez-Montero, Lía; Gotor, Vicente; Gotor-Fernández, Vicente; Lavandera, Iván

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 10 p. 1618 - 1624 Title/Abstract Full Text Show Details

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Rx-ID: 40463173 Find similar reactions

Multi-step reaction with 2 steps 1: copper(l) chloride / tetrahydrofuran / 0.5 h / 46 - 51 °C 2: hydrogenchloride / water / 1.5 h / 80 °C View Scheme

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: copper(l) chloride / tetrahydrofuran / 0.5 h / 48 - 51 °C 2: hydrogenchloride / water / 1 h / 80 °C View Scheme

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: copper(l) chloride / tetrahydrofuran / 0.5 h / 48 - 51 °C 2: hydrogenchloride / water / 12 h / 80 °C View Scheme

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Title/Abstract Full Text Show Details

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Rx-ID: 40463180 Find similar reactions

With hydrogenchloride in water

T=80°C; 1 h; Hide Experimental Procedure

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Location in patent: Paragraph 0122; 0123 ; Title/Abstract Full Text Show Details

Preparation of Dexamphetamine (7) from 5a

Preparation of Dexamphetamine (7) from 5a A 50 mL flask was charged with 5a (4.80 g, 19.73 mmol) and 3 M HCl (15.0 mL) and the stirred reaction mixture was heated to 80° C. for 1 hour, then cooled to room temperature. The reaction mixture was washed with isopropyl acetate (2*20 mL) and the organic extracts were disposed. The aqueous layer was treated with sodium hydroxide solution (50percent, 12.0 mL) keeping the internal temperature below 25° C. Methyl tert-butyl ether (15 mL) was added and the reaction mixture was agitated for 5 minutes then allowed to separate. The organic layer washed with water (10 mL) and concentrated under reduced pressure to give 7 as a colorless oil (2.51 g, 94.4percent yield, >99.5 percent purity by GC and chiral HPLC).

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With hydrogenchloride in water

T=80°C; 1.5 h; Hide Experimental Procedure

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Rx-ID: 40463181 Find similar reactions

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Location in patent: Paragraph 0139; 0140 ;

Title/Abstract Full Text Show Details

Preparation of Dexamphetamine (7) from 5b

Preparation of Dexamphetamine (7) from 5b A 2 L, jacketed, bottom outlet valve flask was charged with 5b (209 g, 0.770 mol) and 3 M hydrochloric acid (510 mL) and the reaction mixture was heated to 80° C. for 1.5 hours and then cooled to room temperature. The orange solution was extracted with isopropyl acetate (500 mL) and the organic extract layer was discarded. Sodium hydroxide solution (50percent, 175 mL) was slowly added to the remaining aqueous layer, keeping the internal temperature below 25° C. Methyl tert-butyl ether (200 mL) was added and the reaction mixture was agitated for 20 minutes then allowed to separate for 30 minutes. The aqueous layer was removed and the organic layer washed with water (100 mL) and concentrated under reduced pressure to afford a light brown oil, This oil was distilled (Distillation conditions: 1" wipe film still, T=65-90° C., vacuum=4-5 mmHg, wiper speed=490-520 rpm.) to give dexamphetamine (7) as a clear colorless oil (81 g, 78percent yield; >99.8percent pure by GC). Chiral HPEC analysis: 99.83percent dextroampehtamine; 0.16percent levoamphetamine; 99.67percent cc. Optical rotation c=2.0, methanol, 22.0° C., +29.2°. ‘H NMR (300 MHz, CDC13) ö 7.36 -7.26 (m, 2H), 7.23-7.13 (m, 3H), 3.26-3.03 (m, 1H), 2.72 (dd, J=13.2, 5.4 Hz, 1H), 2.53 (dd, J=13.2, 8.0 Hz, 1H), 1.20 (br s, 2H), 1.13 (d, J=6.3 Hz, 3H).

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Rx-ID: 40463186 Find similar reactions

With hydrogenchloride in water

T=80°C; 12 h; Hide Experimental Procedure

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Location in patent: Paragraph 0143; 0144 ; Title/Abstract Full Text Show Details

Preparation of Dexamphetamine (7) from 5c

Preparation of Dexamphetamine (7) from 5c A 50 mL flask was charged with 5c (3.54 g, 11.82 mmol) and 3 M HCl (8.7 mL) and the stirred reaction mixture was heated to 80° C. for 12 hours, then cooled to room temperature. The aqueous solution was washed with isopropyl acetate (2*20 mL) and the organic extract was discarded. The aqueous layer was treated with sodium hydroxide solution (50percent, 3.0 mL) keeping the internal temperature below 25° C. Methyl tert-butyl ether (40 mL) was added and the reaction mixture was agitated for 5 minutes then allowed to separate for 15 minutes. The aqueous layer was extracted with methyl tert-butyl ether (40 mL) and the combined organic layers were washed with water (10 mL) and concentrated under reduced pressure to give 7 as a colorless oil (1.28 g, 80.3percent yield, >98.7 percent purity by GC and chiral HPLC).

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With hydrogenchloride in water

T=80°C; 32 h; Hide Experimental Procedure

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Rx-ID: 40463187 Find similar reactions

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Location in patent: Paragraph 0147; 0148 ; Title/Abstract Full Text Show Details

Preparation of Dexamphetamine (7) from 5d

Preparation of Dexamphetamine (7) from 5d A 50 mL flask was charged with 5d (7.24 g, 19.71 mmol) and 3 M HCl (15.0 mL) and the stirred reaction mixture was heated to 80° C. for 32 hours, at which point it was cooled to room temperature. The organic layer was washed with isopropyl acetate (2*20 mL) and the organic extracts were discarded. The aqueous layer was treated with sodium hydroxide solution (50percent, 3.0 mL) keeping the internal temperature below 25° C. Methyl tert-butyl ether (40 mL) was added and the reaction mixture was agitated for 5 minutes and then separated. A second portion of methyl tert-butyl ether (40 mL) was added and the reaction mixture was agitated for 5 minutes. The combined organic extracts were washed with water (10 mL) and concentrated under reduced pressure to give 7 as a colorless oil (2.05 g, 76.9percent yield, >99percent GC purity).

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Synthesize Find similar Rx-ID: 9202054 Find similar reactions

Stage #1: With (S)-isopropylidene glycerol 3-carboxy-2-naphthoate in methanol

T=20°C; Stage #2: With sulfuric acid in ethyl acetate

Title compound not separated from byproducts;

Pallavicini, Marco; Bolchi, Cristiano; Fumagalli, Laura; Valoti, Ermanno; Villa, Luigi

Tetrahedron Asymmetry, 2002 , vol. 13, # 20 p. 2277 - 2282 Title/Abstract Full Text View citing articles Show Details

With column LiChrospher 100 RP-18e; sulfated β-cyclodextrin in methanol; water

T=20°C; Reagent/catalyst;

Taschwer, Magdalena; Seidl, Yvonne; Mohr, Stefan; Schmid, Martin G.

Chirality, 2014 , vol. 26, # 8 p. 411 - 418 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 38266824 Find similar reactions

Multi-step reaction with 3 steps 1: N-butylamine; acetic acid / 60 °C / |Sonication 2: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C / |Cooling with ice 3: hydrogen; palladium 10 on activated carbon / methanol / 3800.26 Torr View Scheme

Li, Shengkun; Huang, Kexuan; Zhang, Xumu

Chemical Communications, 2014 , vol. 50, # 64 p. 8878 - 8881 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 38266844 Find similar reactions

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Multi-step reaction with 2 steps 1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C / |Cooling with ice 2: hydrogen; palladium 10 on activated carbon / methanol / 3800.26 Torr View Scheme

Li, Shengkun; Huang, Kexuan; Zhang, Xumu

Chemical Communications, 2014 , vol. 50, # 64 p. 8878 - 8881 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 38266867 Find similar reactions

With palladium 10 on activated carbon; hydrogen in methanol

P=3800.26 Torr; Overall yield = 94 percent;

Li, Shengkun; Huang, Kexuan; Zhang, Xumu

Chemical Communications, 2014 , vol. 50, # 64 p. 8878 - 8881 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13217142 Find similar reactions

Multi-step reaction with 7 steps 1: 90 percent / bakers' yeast; Tween 80; aq. sucrose / 25 - 32 °C 2: 85 percent / 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 3: triethylamine / 3 h / 75 - 80 °C 4: aq. LiOH / methanol / 3 h / 20 °C 5: 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 6: 97 percent / sodium azide / dimethylsulfoxide / 2 h / 45 °C 7: 99 percent / H2 / Pd/C / ethyl acetate / 12 h / 20 °C / 912 Torr View Scheme

Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei

Journal of Chemical Research, 2004 , # 10 p. 681 - 683 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 190 °C / Erhitzen des Reaktionsprodukts mit wss.Schwefelsaeure auf 125grad 2: Gewinnung ueber das Lg-Hydrogentartrat View Scheme

Magidson; Garkuscha

Zhurnal Obshchei Khimii, 1941 , vol. 11, p. 339,341 Chem.Abstr., 1941 , p. 5868 Full Text Show Details

Multi-step reaction with 3 steps 1: titanium(IV) isopropylate; ammonia / methanol / 6 h / 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 3 h / 20 °C 3: Candida antartica lipase B; triethylamine / n-heptane / 2.6 h / 35 °C / Inert atmosphere; Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: titanium(IV) isopropylate; ammonia / methanol / 6 h / 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 3 h / 20 °C 3: Candida antartica lipase B; methoxy acetic acid ethyl ester; triethylamine / 35 °C / Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

With phosphoric acid; pyridoxal 5'-phosphate; ω-transaminase (S)-TA from Pseudomonas aeruginosa; 1-amino-1-phenylethane

T=30°C; pH=7.5; 24 h; Enzymatic reaction; Reagent/catalyst; enantioselective reaction; Hide Experimental Procedure

Fesko, Kateryna; Steiner, Kerstin; Breinbauer, Rolf; Schwab, Helmut; Schuermann, Martin; Strohmeier, Gernot A.

Journal of Molecular Catalysis B: Enzymatic, 2013 , vol. 96, p. 103 - 110 Title/Abstract Full Text View citing articles Show Details

2.3 General procedure for ω-transaminase catalyzed reactions

Sodium phosphate reaction buffer (50mM, pH 7.5) containing 0.1mM PLP was mixed with the ketone substrate (10 or 50mM) and the appropriate amino donor (0.1–0.5M). The pH was adjusted to 7.5 with phosphoric acid before adding the enzymes. The reactions were started by adding 50μl of cell-free extract (CFE, contains approximately 2mg of protein) and then shaken at 30°C for 24h.

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Rx-ID: 35972128 Find similar reactions

With sodium hydroxide

Thornton, Melissa; Chickos, James; Garist, Inna V.; Varfolomeev, Mikhail A.; Svetlov, Aleksei A.; Verevkin, Sergey P.

Journal of Chemical and Engineering Data, 2013 , vol. 58, # 7 p. 2018 - 2027 Title/Abstract Full Text View citing articles Show Details

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92%

With ammonium hydroxide in water

Hide Experimental Procedure

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Rx-ID: 32483502 Find similar reactions

King, Clifford Riley; D'Ambrosio, Stephen G.; Bristol, David W.

Patent: US2012/28960 A1, 2012 ; Location in patent: Page/Page column 24-25 ; Title/Abstract Full Text Show Details

To a 200 mL beaker equipped with a magnetic stir bar was charged 5.0 g (13.6 mmol) dextro-amphetamine sulfate and 50 mL water to dissolve the solid. Ammonium hydroxide (2.5 g; 70.7 mmol) was then added and the solution remained clear and colorless. The solution was subsequently extracted with three 50 mL portions of ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum at 50° C. to provide 3.4 g (92percent) of a clear colorless oil. The FTIR spectrum of the free base was consistent with the intended structure.

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Rx-ID: 33148356 Find similar reactions

With ammonium sulfate in 2,4-dimethylbutane; water

T=30°C; pH=10; 96 h; Product distribution / selectivity; Hide Experimental Procedure

BASF SE

Patent: US2012/123155 A1, 2012 ; Location in patent: Page/Page column 11 ; Title/Abstract Full Text Show Details

5) Reaction; Whole cells of (Rt)-PAL or (Pc)-PAL (300 mg) were added to trans-β-methylstyrene (10 mM) in a 4 M ammonium hydroxide solution (pH 10, 10 mL total volume). The reaction mixture was incubated for 4 d at 30° C. and 250 rpm. The pH was readjusted to 12 with 5 M NaOH and extracted with 4 mL CH2Cl2. The organic layer was filtered and evaporated. The precipitate was dissolved in a H2O/acetonitrile mixture containing 0.1percent formic acid (70/30, 500 μL) and injected to the LC-MS system (FIG. 3/4). 6) Product Identification by LC-MS; LC-MS analysis was performed by using API-ES ionisation in both positive and negative mode. An Exclipse-XDE C18 5μ column (5 μm, 4.6.x.150 mm) was used for analytical separation. The flow rate was 0.5 mL/min and the temperature of the column was maintained at 15° C. Propiophenone (1 μL/mL) was used as internal standard for determining the conversion of reaction. Products obtained from trans-β-methylstyrene biotransformations were eluted with a gradient as follows: start with 10/90 acetonitrile/H2O for 12 min, in 10 min from 10/90 to 40/60 and from 40/60 to 10/90 from 22 min to 30 min. The analyses were carried out with UV detection at 220 and 260 nm. 7) Reaction Using Diverse Substrates; Whole cells of (Rt)-PAL (300 mg) were added to substrate (10 mM) in a 4 M ammonium sulfate solution (pH 10, iso-Hexan, 10 mL total volume). The reaction mixture was incubated for 4 d at 30° C. and 250 rpm. The pH was readjusted to 12 with 5 M NaOH and extracted with 4 mL CH2Cl2. The organic layer was filtered and evaporated. The precipitate was dissolved in a H2O/acetonitrile mixture containing 0.1percent formic acid (70/30, 500 μL) for all others and injected to the LC-MS system. 8) Determination of Enantiomeric Excess of Product; For the determination of the enantiomeric excess, the amine formed during biotransformation of trans-beta-methylstyrene was derivatised (Ac2O, DMAP, EtOAc) to obtain the corresponding acetylated amine in order to achieve enantioseparation on a chiral GC column. An aliquot of the enzyme reaction mixture (0.5 mL) was extracted with 0.5 mL of ethyl acetate and dried over Na2SO4. After addition of 0.5 mL of acetic anhydride and cat. DMAP, the Eppendorff vial was shaken at rt for 30 min. The samples were extracted with 0.5 mL of water, the organic phase was dried over Na2SO4 and the samples were analysed on chiral GC-FID. GC analyses were carried out on an Agilent 6850 Network gas chromatograph equipped with FID and a Gerstel MPS2L multipurpose autosampler using a Varian CPChirasil-DEX CB column (25 m.x.0.25 mm.x.0.25 μm film) and H2 as carrier gas. The injector temperature is set 250° C. with a flow of 1.7 ml/min H2 and a temperature program of 150° C.-hold 10 min-15° C./min-180° C.-hold 5 min-15° C./min-250° C. Hydroamination of trans-beta-methylstyrene using different ammonia sources A

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Rx-ID: 33556077 Find similar reactions

B: 21%

With coated protease in 3-methyl pentan-3-ol

T=21°C; 72 h; Resolution of racemateEnzymatic reaction; enantioselective reaction;

Queyroy, Severine; Vanthuyne, Nicolas; Gastaldi, Stephane; Bertrand, Michele P.; Gil, Gerard

Advanced Synthesis and Catalysis, 2012 , vol. 354, # 9 p. 1759 - 1764 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 436360 Find similar reactions

63%

With methoxy acetic acid ethyl ester; Candida antartica lipase B; triethylamine

T=35°C; Enzymatic reaction; optical yield given as percent ee;

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

Gewinnung ueber das Lg-Hydrogentartrat;

Magidson; Garkuscha

Zhurnal Obshchei Khimii, 1941 , vol. 11, p. 339,341 Chem.Abstr., 1941 , p. 5868 Full Text Show Details

Leithe

Chemische Berichte, 1932 , vol. 65, p. 660,665 Full Text Show Details

Jaeger; van Dijk

Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1941 , vol. 44, p. 26,36,37 Full Text Show Details

With L-(+)-tartaric acid

Gewinnung;

Potapow; Terentew

Zhurnal Obshchei Khimii, 1958 , vol. 28, p. 3323,3325 Anm. J. Gen. Chem. USSR (Engl. Transl.), 1958 , vol. 28, p. 3349,3351 Anm. Full Text Show Details

Pratesi; La Manna

Farmaco, Edizione Scientifica, 1956 , vol. 11, p. 33,41 Full Text Show Details

Murakami; Akagi

Nippon Kagaku Zasshi, 1954 , vol. 75, p. 532,534 Chem.Abstr., 1957 , p. 11242 Full Text Show Details

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Rx-ID: 18560093 Find similar reactions

Multi-step reaction with 2 steps 1: H2O / 48 h / 30 °C / microbial reduction with Rhodococcus rhodochrous IFO 3338 2: Iron, ferrous sulfate heptahydrate / acetic acid View Scheme

Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi

Agricultural and Biological Chemistry, 1985 , vol. 49, # 8 p. 2331 - 2336 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: H2O / 48 h / 30 °C / microbial reduction with Rhodococcus rhodochrous IFO 3338 2: Iron powder, ferrous sulfate hezahydrate / acetic acid View Scheme

Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi

Agricultural and Biological Chemistry, 1985 , vol. 49, # 8 p. 2331 - 2336 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 3 h / Inert atmosphere; Reflux 2: Candida antartica lipase B; triethylamine / n-heptane / 2.6 h / 35 °C / Inert atmosphere; Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

Hide Details

Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 3 h / Inert atmosphere; Reflux 2: Candida antartica lipase B; methoxy acetic acid ethyl ester; triethylamine / 35 °C / Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 31607345 Find similar reactions

With supported Candida antartica lipase B in tert-butyl methyl ether

T=38 - 40°C; 6 h; Molecular sieveEnzymatic reaction; optical yield given as percent eeenantioselective reaction;

Poulhes, Florent; Vanthuyne, Nicolas; Bertrand, Michele P.; Gastaldi, Stephane; Gil, Gerard

Journal of Organic Chemistry, 2011 , vol. 76, # 17 p. 7281 - 7286 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 32451798 Find similar reactions

B: 47%

With Candida antartica lipase B; triethylamine in n-heptane

T=35°C; 2.6 h; Inert atmosphereEnzymatic reaction; optical yield given as percent ee;

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 32451892 Find similar reactions

Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 3 h / 20 °C 2: Candida antartica lipase B; triethylamine / n-heptane / 2.6 h / 35 °C / Inert atmosphere; Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 3 h / 20 °C 2: Candida antartica lipase B; methoxy acetic acid ethyl ester; triethylamine / 35 °C / Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 32451927 Find similar reactions

Multi-step reaction with 3 steps 1: ammonium acetate / Reflux 2: lithium aluminium tetrahydride / diethyl ether / 3 h / Inert atmosphere; Reflux 3: Candida antartica lipase B; triethylamine / n-heptane / 2.6 h / 35 °C / Inert atmosphere; Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: ammonium acetate / Reflux 2: lithium aluminium tetrahydride / diethyl ether / 3 h / Inert atmosphere; Reflux 3: Candida antartica lipase B; methoxy acetic acid ethyl ester; triethylamine / 35 °C / Enzymatic reaction View Scheme

Munoz, Lourdes; Rodriguez, Anna M.; Rosell, Gloria; Bosch, M. Pilar; Guerrero, Angel

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 23 p. 8171 - 8177 Title/Abstract Full Text View citing articles Show Details

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94%

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With hydrogen; palladium 10 on activated carbon in methanol; ethanol

T=20°C; 4 h; Product distribution / selectivity; Hide Experimental Procedure

Rx-ID: 29359101 Find similar reactions

Johnson Matthey Public Limited Company

Patent: US2010/125146 A1, 2010 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details

1:Dextroamphetamine

EXAMPLE 1 Dextroamphetamine A mixture of 6.00 g (33.9 mmol) (4S,5R)-(-)-4-methyl-5-phenyl-2-oxazolidinone, 0.34 g 10percent palladium-on-carbon (50percent water wet), and 60 mL SDA-3A (a solvent constituting 95percent Ethanol and 5percent Methanol) was stirred under a hydrogen filled balloon at ambient temperature (approximately 20° C.) until no more oxazolidinone was detected by HPLC, 4 h. The reaction mixture was then filtered through a pad of Celite to remove the catalyst. For the purposes of isolating the free base, a filtered reaction mixture was carefully concentrated under reduced pressure to leave 4.47 g of a crystalline semi-solid, which was found to be a mixture of 96percent dextroamphetamine and 4percent ethanol by 1H NMR. Some dextroamphetamine was detected in the distillate. Yield=94percent. 400 MHz 1H NMR (CDCl3) 7.34-7.20 (m, 5), 3.22-3.17 (m, 1), 2.76-2.72 (d of d, J=13.2 Hz, J'=5.4 Hz, 1), 2.57-2.52 (d of d, J=13.2 Hz, J'=8.1 Hz, 1), 1.16-1.14 (d, J=6.3 Hz, 3).

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Rx-ID: 29831496 Find similar reactions

With sodium hydroxide in dichloromethane; water

pH=9 - 10; Hide Experimental Procedure

ARCHIMICA, INC.; MEUDT, Andreas; WISDOM, Richard; HELMKE, Jason; QIU, Guofang; MEENK, Paul

Patent: WO2010/42120 A1, 2010 ; Location in patent: Page/Page column 8-10 ; Title/Abstract Full Text Show Details

Boc-Lys(Boc)-OH D-Amphetamine MW: 463.62 dicyclohexylammonium salt Sulfate saltCAS 15908-69-8 CAS 51-63-8 MW: 368.49MW: 527.74L-Iysine-d-amphetamine dimesyiate was synthesized by T3P coupling of Di- Boc-L-Lysine free acid with D-amphetamine free base:Preparation of the free acid of Di-N-Boc-L-Lysine: Di-N-BocL-Lysine dicyclohexylammonium salt (2.Og, 3.8mmol) was taken up with 75ml of EtOAc, partitioned with 75ml of Dl water, and washed with 75ml 1 N HCI. The aqueous layer was extracted with 50ml of EtOAc and the combined organic layers were washed with 2 χ75ml of 1 N HCI and 75ml of brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure.Preparation of D-amphetamine free base: D-amphetamine sulfate (0.7g, 1.9mmol) was taken up with 15ml of MDC and partitioned with 10ml of Dl water. The mixture was basified with 10percent NaOH aq. solution to pH 9-10. The aqueous layer was extracted with 2* 10ml of MDC. The combined organic layers were dried over MgSO4, filtered, and evaporated to dryness.T3P Coupling of L-Iysine free acid with D-amphetamine free base: - -To a solution of Di-N-Boc-L-Lysine free acid (1.3g, 3.8mmol, 1eq) in 10ml EtOAc under N2 was added DIPEA (1.5g, 11.4mmol, 3eq) and the resulting mixture was allowed to stir at room temperature for 10 min. A solution of D-amphetamine free base (0.5g, 3.8mmol, 1eq) in 5ml EtOAc was added and the mixture stirred at ambient temperature for 20 min. T3P solution in EtOAc (52.7percent w/w, 3.Og, 4.9mmol, 1.3 eq) was added slowly at 20-250C while cooling the flask externally with an ice/water bath. The reaction mixture was stirred for 1-2 hours at 20-250C which resulted in reaction completion. Upon reaction completion, 10g of water were added while keeping the temperature <25°C. After mixing for 15 min, the aqueous layer was extracted with (2x1 OmI) EtOAc. The combined organic phases were washed with saturated NaHCO3 (2χ15ml) aqueous solution, and then 15ml of brine. The organic layer was filtered and evaporated to dryness yielding the white solid Di-Boc- Lys-AmpDeprotection and preparation of mesylate salt:A 50ml flask was charged with Di-Boc-Lys-Amp white solid, (1.76g, 3.8mmol, 1eq) and 1 ,4-dioxane (15.0 ml) and the mixture was stirred rapidly under N2 for 30 min. The resulting solution was filtered and the filter cake was rinsed with 1 ,4-dioxane (2χ1. OmI). To the combined filtrates (clear, slightly yellow solution) was added methanesulfonic acid (1.83g, 19.0mmol, 5eq) over 1 hour while keeping the internal

temperature at 21+/-3°C. Approximately 1 hour after the addition was completed, a white precipitate began to appear. The mixture was stirred at ambient temperature - -for 20.5 hours and until HPLC monitoring indicated the disappearance of all starting material. The slurry was filtered through filter paper and the flask was rinsed with 1 8ml of 1 , 4-dioxane. The filter-cake was washed with 1 , 4-dioxane (3x1.8mL) and then dried under vacuum at 55°C for ~90h. This afforded Lys-Amp dimesylate as a white solid. A

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With lithium hydroxide hydrate in N,N-dimethyl-formamide

T=20°C; Inert atmosphere;

Bornholdt, Jan; Felding, Jakob; Clausen, Rasmus P.; Kristensen, Jesper L.

Chemistry - A European Journal, 2010 , vol. 16, # 41 p. 12474 - 12480 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 28864998 Find similar reactions

With hydrogen; sodium acetate; acetic acid; palladium 10 on activated carbon in water

T=20°C; P=775.743 Torr; 26 h; Product distribution / selectivity; Hide Experimental Procedure

Cambrex Charles City

Patent: US2009/292143 A1, 2009 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details

EXAMPLE 4HydrogenationInto a glass vessel with magnetic stirring, 4.12 g of a crude D-chloroamphetamine hydrochloride was charged (prepared per Example 1), along with 10 g of water, and 0.42 g of carbon. The carbon slurry was filtered through Celatom to clarify. Then 0.25 g of a 10 wt percent Pd/C catalyst (50 wt percent water wet) was charged into the vessel along with 3.6 g sodium acetate, and 8.5 g acetic acid. The vessel was purged with hydrogen and stirred at 20° C. under a hydrogen atmospheric at about 15 psi (e.g., balloon pressurized hydrogen atmosphere). The extent of the reaction was monitored by HPLC analysis. After 3.5 hours, the reaction was 20percent complete. After 26 hours, the reaction was >99percent complete.

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Rx-ID: 29475647 Find similar reactions

With palladium 10 on activated carbon; hydrogen; triethylamine

48 h;

Lamb, Pamela B.; McElhinny, Charles J.; Sninski, Todd; Purdom, Hunter; Carroll, F. Ivy; Lewin, Anita H.

Journal of Labelled Compounds and Radiopharmaceuticals, 2009 , vol. 52, # 11 p. 457 - 462 Title/Abstract Full Text View citing articles Show Details

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With recombinant human acetylcholinesterase

T=37°C; Kinetics;

Verheijen, Jeroen C.; Wiig, Kjesten A.; Du, Shoucheng; Connors, Stacie L.; Martin, Ashley N.; Ferreira, Jennifer P.; Slepnev, Vladimir I.; Kochendoerfer, Ulrike

Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 12 p. 3243 - 3246 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3606560 Find similar reactions

With sodium hydroxide

Smith, Roger A.; White, Robert L.; Krantz, Allen

Journal of Medicinal Chemistry, 1988 , vol. 31, # 8 p. 1558 - 1566 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

pH=10.5 - 12.5; Product distribution / selectivity; Hide Experimental Procedure

CAMBREX CHARLES CITY, INC.

Patent: WO2007/41571 A1, 2007 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details

1; 2:

Water (960 ml) was added to a reaction vessel containing 12O g ^-amphetamine sulfate (mw 368.49). The pH was adjusted to not less than 12.5 using 50percent sodium hydroxide (61 g). Isopropyl acetate (522 g) was added to the d-amphetamine solution. The aqueous phase was removed and extracted with isopropyl acetate. Remaining water was then removed by exposing the isopropyl acetate solution to MgSO4; EXAMPLE 2[11] Water (960 ml) was added to a reaction vessel containing 12O g d-amphetamine sulfate (mw 368.49). TheψH was adjusted tσ~ t5=i 1.5 using 50percent sodium hydroxide (61 g). Isopropyl acetate (522 g) was added to the ^-amphetamine solution. The aqueous phase was removed and extracted with isopropyl acetate. Remaining water was then removed by exposing the isopropyl acetate solution to a sodium chloride solution. A

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Rx-ID: 11152133 Find similar reactions

A: 46% B: 27%

With Candida antarctica lipase B in n-heptane

T=80°C; 9 h;

Nechab, Malek; Azzi, Nadia; Vanthuyne, Nicolas; Bertrand, Michele; Gastaldi, Stephane; Gil, Gerard

Journal of Organic Chemistry, 2007 , vol. 72, # 18 p. 6918 - 6923 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9785510

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With sulfuric acid

40 h; Heating;

Fecik, Robert A.; Devasthale, Pratik; Pillai, Segaran; Keschavarz-Shokri, Ali; Shen, Linus; Mitscher, Lester A.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 4 p. 1229 - 1236 Title/Abstract Full Text View citing articles Show Details

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84%

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Rx-ID: 9914950 Find similar reactions

With hydrazine in methanol

Heating;

Barrett, David G.; Deaton, David N.; Hassell, Anne M.; McFadyen, Robert B.; Miller, Aaron B.; Miller, Larry R.; Payne, J. Alan; Shewchuk, Lisa M.; Willard Jr., Derril H.; Wright, Lois L.

Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 12 p. 3039 - 3043 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9969517 Find similar reactions

A: 43%

With Candida antarctica lipase in di-isopropyl ether

T=30°C; 30 h;

Yang, Bo; Zhang, Yanjun; Zhang, Shusheng; Izumi

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005 , vol. 44, # 6 p. 1312 - 1316 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps

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Rx-ID: 12887588 Find similar reactions

Barrett, David G.; Deaton, David N.; Hassell, Anne M.; McFadyen, Robert B.; Miller, Aaron B.; Miller, Larry R.; Payne, J. Alan;

Shewchuk, Lisa M.; Willard Jr., Derril H.; Wright, Lois L.

Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 12 p. 3039 - 3043 Title/Abstract Full Text View citing articles Show Details

1: 93 percent / DEAD; Ph3P / tetrahydrofuran 2: 84 percent / N2H4 / methanol / Heating View Scheme

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Rx-ID: 13205671 Find similar reactions

Multi-step reaction with 3 steps 1: 95 percent / pyridine / 24 h / 20 °C 2: 55 percent / H2; aq. perchloric acid; glacial AcOH / Pd/BaSO4 / 4.5 h / 95 °C / atmospheric pressure 3: aq. H2SO4 / 40 h / Heating View Scheme

Fecik, Robert A.; Devasthale, Pratik; Pillai, Segaran; Keschavarz-Shokri, Ali; Shen, Linus; Mitscher, Lester A.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 4 p. 1229 - 1236 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13219306 Find similar reactions

Multi-step reaction with 2 steps 1: 55 percent / H2; aq. perchloric acid; glacial AcOH / Pd/BaSO4 / 4.5 h / 95 °C / atmospheric pressure 2: aq. H2SO4 / 40 h / Heating View Scheme

Fecik, Robert A.; Devasthale, Pratik; Pillai, Segaran; Keschavarz-Shokri, Ali; Shen, Linus; Mitscher, Lester A.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 4 p. 1229 - 1236 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9739156 Find similar reactions

Stage #1: With sodium azide in N,N-dimethyl-formamide

T=80°C; 6 h; Stage #2: With triphenylphosphine in acetonitrile

6 h; Heating; Stage #3: With ammonium formate; palladium on activated charcoal in methanol

4 h; Heating; Title compound not separated from byproducts;

Sayyed, Iliyas Ali; Sudalai, Arumugam

Tetrahedron Asymmetry, 2004 , vol. 15, # 19 p. 3111 - 3116 Title/Abstract Full Text View citing articles Show Details

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99%

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Rx-ID: 9820983 Find similar reactions

With hydrogen; palladium on activated charcoal in ethyl acetate

T=20°C; P=912 Torr; 12 h;

Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei

Journal of Chemical Research, 2004 , # 10 p. 681 - 683 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13206939 Find similar reactions

Multi-step reaction with 6 steps 1: 85 percent / 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 2: triethylamine / 3 h / 75 - 80 °C 3: aq. LiOH / methanol / 3 h / 20 °C 4: 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 5: 97 percent / sodium azide / dimethylsulfoxide / 2 h / 45 °C 6: 99 percent / H2 / Pd/C / ethyl acetate / 12 h / 20 °C / 912 Torr View Scheme

Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei

Journal of Chemical Research, 2004 , # 10 p. 681 - 683 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13206961 Find similar reactions

Multi-step reaction with 4 steps 1: aq. LiOH / methanol / 3 h / 20 °C 2: 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 3: 97 percent / sodium azide / dimethylsulfoxide / 2 h / 45 °C 4: 99 percent / H2 / Pd/C / ethyl acetate / 12 h / 20 °C / 912 Torr View Scheme

Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei

Journal of Chemical Research, 2004 , # 10 p. 681 - 683 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13208335 Find similar reactions

Multi-step reaction with 3 steps 1: 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 2: 97 percent / sodium azide / dimethylsulfoxide / 2 h / 45 °C 3: 99 percent / H2 / Pd/C / ethyl acetate / 12 h / 20 °C / 912 Torr View Scheme

Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei

Journal of Chemical Research, 2004 , # 10 p. 681 - 683 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 13208399 Find similar reactions

Multi-step reaction with 2 steps 1: 97 percent / sodium azide / dimethylsulfoxide / 2 h / 45 °C 2: 99 percent / H2 / Pd/C / ethyl acetate / 12 h / 20 °C / 912 Torr View Scheme

Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei

Journal of Chemical Research, 2004 , # 10 p. 681 - 683 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 5 steps

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Rx-ID: 13208400 Find similar reactions

Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei

1: triethylamine / 3 h / 75 - 80 °C 2: aq. LiOH / methanol / 3 h / 20 °C 3: 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 4: 97 percent / sodium azide / dimethylsulfoxide / 2 h / 45 °C 5: 99 percent / H2 / Pd/C / ethyl acetate / 12 h / 20 °C / 912 Torr View Scheme

Journal of Chemical Research, 2004 , # 10 p. 681 - 683 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1.1: 85 percent / triethylamine; thionyl chloride / 0.75 h / 0 °C 2.1: sodium azide / dimethylformamide / 6 h / 80 °C 2.2: PPh3 / acetonitrile / 6 h / Heating 2.3: ammonium formate / Pd/C / methanol / 4 h / Heating View Scheme

Rx-ID: 13429258 Find similar reactions

Sayyed, Iliyas Ali; Sudalai, Arumugam

Tetrahedron Asymmetry, 2004 , vol. 15, # 19 p. 3111 - 3116 Title/Abstract Full Text View citing articles Show Details

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59%

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Rx-ID: 7361624 Find similar reactions

Lederman, Seth; Levensr, Steve; Kucharik JR., Robert

Patent: US2003/96004 A1, 2003 ; Title/Abstract Full Text Show Details

2:Step 3-(+)-Amphetamine

Step 3-(+)-Amphetamine Norchloroephedrine hydrochloride was reduced by placing a suspension of sodium acetate and norchloroephedrine hydrochloride in glacial acetic acid (207 milliliters) and distilled water (10.8 milliliters) in a Parr bomb under 50 psi of hydrogen with 5percent palladium on barium sulfate as a catalyst. The reaction was complete when the uptake of hydrogen ceased. The reaction was also monitored by gas chromatography. The reaction was filtered through celite and washed with distilled water. The majority of glacial acetic acid was then removed in vacuo. The pH of the product was increased to 10 with an aqueous 10percent sodium hydroxide solution, extracted three times with ethyl ether, dried on sodium sulfate, and concentrated. The crude product was purified by fractional distillation under reduced pressure (1 mm Hg) to produce 9.6 grams of (+)-amphetamine at 99percent purity (59percent yield).

Busser,U.; Haller,R.

Tetrahedron Letters, 1973 , p. 231 - 232 Full Text View citing articles Show Details

Repke et al.

Journal of Pharmaceutical Sciences, 1978 , vol. 67, p. 1167,1168 Full Text Show Details

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Rx-ID: 9134594 Find similar reactions

With bis-[(trifluoroacetoxy)iodo]benzene in water; acetonitrile

T=20°C; Hofmann degradation; 5 h;

Davies, Stephen G.; Dixon, Darren J.

Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 16 p. 1869 - 1876 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9200911 Find similar reactions

With Candida antarctica lipase B

T=28°C; 7 h;

Gonzalez-Sabin, Javier; Gotor, Vicente; Rebolledo, Francisca

Tetrahedron Asymmetry, 2002 , vol. 13, # 12 p. 1315 - 1320 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 22871540 Find similar reactions

With hydrogenchloride in water

Yamakawa Chemical Industry Co., Ltd.

Patent: US6342636 B1, 2002 ; Location in patent: Example 15 ;

Title/Abstract Full Text Show Details

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Rx-ID: 8825466 Find similar reactions

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With Candida antarctica (Novozym 435) in diethyl ether

T=21°C; 48 h; Enzymatic reaction; Title compound not separated from byproducts;

Davis; Durden

Synthetic Communications, 2001 , vol. 31, # 4 p. 569 - 578 Title/Abstract Full Text View citing articles Show Details

With Candida antarctica (Novozym 435)

T=21°C; 240 h; Enzymatic reaction; Title compound not separated from byproducts;

Davis; Durden

Synthetic Communications, 2001 , vol. 31, # 4 p. 569 - 578 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3507397 Find similar reactions

With hydrazine hydrate in butan-1-ol

2 h; Heating;

Rozwadowska

Tetrahedron Asymmetry, 1993 , vol. 4, # 7 p. 1619 - 1624 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: 88 percent / 160 °C 2: 86 percent / PPh3, I2 / toluene / 1 h / Heating 3: 94 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 20 h / 1140 Torr 4: 80percent aq. hydrazine / butan-1-ol / 2 h / Heating

Rx-ID: 18940750 Find similar reactions

Rozwadowska

Tetrahedron Asymmetry, 1993 , vol. 4, # 7 p. 1619 - 1624 Title/Abstract Full Text View citing articles Show Details

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View Scheme

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Rx-ID: 18942680 Find similar reactions

Multi-step reaction with 3 steps 1: 86 percent / PPh3, I2 / toluene / 1 h / Heating 2: 94 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 20 h / 1140 Torr 3: 80percent aq. hydrazine / butan-1-ol / 2 h / Heating View Scheme

Rozwadowska

Tetrahedron Asymmetry, 1993 , vol. 4, # 7 p. 1619 - 1624 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 18945691 Find similar reactions

Multi-step reaction with 2 steps 1: 94 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 20 h / 1140 Torr 2: 80percent aq. hydrazine / butan-1-ol / 2 h / Heating View Scheme

Rozwadowska

Tetrahedron Asymmetry, 1993 , vol. 4, # 7 p. 1619 - 1624 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 3109208 Find similar reactions

enantioselective biotransformation on rats; determined in 24 h urine;

Harsche; Oelschlaeger; Engel

Archiv der Pharmazie, 1992 , vol. 325, # 9 p. 593 - 595 Title/Abstract Full Text View citing articles Show Details

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65%

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Rx-ID: 2199671 Find similar reactions

With potassium carbonate in methanol; water

Nordlander, J. Eric; Njoroge, F. George; Payne, Mark J.; Warman, Dhiraj

Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3481 - 3484 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 3703793 Find similar reactions

With iron; iron(II) sulfate in acetic acid

Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi

Agricultural and Biological Chemistry, 1985 , vol. 49, # 8 p. 2331 - 2336 Title/Abstract Full Text Show Details

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With iron; iron(II) sulfate in acetic acid

Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi

Agricultural and Biological Chemistry, 1985 , vol. 49, # 8 p. 2331 - 2336 Title/Abstract Full Text Show Details

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Rx-ID: 19803890 Find similar reactions

Multi-step reaction with 2 steps 1: 71 percent / H2 / 10percent Pd/C / trifluoroacetic acid / 54 h / 2844.3 Torr 2: 65 percent / K2CO3 / methanol; H2O View Scheme

Nordlander, J. Eric; Njoroge, F. George; Payne, Mark J.; Warman, Dhiraj

Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3481 - 3484 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 2962564 Find similar reactions

With lithium aluminium tetrahydride; 3-O-cyclohexylmethyl-1,2-O-cyclohexylidene-α-D-glucofuranose in diethyl ether

2.5 h; HeatingLiAlH4 concentration effect on enantiomeric excess; asymmetric reduction of ketones and isoelectronic ketone oximes with LiAlH4-3-O-cyclohexylmethyl1,2-O-cyclohexylidene-α-D-glucofuranose complex; Product distribution;

Landor, Stephen R.; Chan, Yuet M.; Sonola, Olutunji O.; Tatchell, Austin R.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , # 3 p. 493 - 496 Title/Abstract Full Text View citing articles Show Details

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With sulfuric acid in water

2 h; Ambient temperature; Yield given;

Ikota; Achiwa; Yamada