Reaxys
PubChem
eMolecules
Reactions (28)
Yield
Substances (6)
Citations (15)
Conditions
References
1
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Rx-ID: 156491 Find similar reactions
Jacquier; Christol
Bulletin de la Societe Chimique de France, 1957 , p. 600,606 Full Text Show Details
With methanol; ammonia; nickel
T=120°C; P=73550.8 Torr; Hydrogenation;
2
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Rx-ID: 332073
Find similar 89%
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With hydrogen; platinum(IV) oxide in acetic acid
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
With hydrogenchloride; ethanol; platinum
T=50°C; Hydrogenation;
Leithe
Chemische Berichte, 1932 , vol. 65, p. 660,665 Full Text Show Details
3
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Rx-ID: 436363 Find similar reactions
With perchloric acid; palladium; acetic acid
T=80 - 90°C; Hydrogenation;
Kindler; Hedemann; Schaerfe
Justus Liebigs Annalen der Chemie, 1948 , vol. 560, p. 215,219 Full Text Show Details
With acetic acid; platinum
Hydrogenation;
Zenitz; Macks; Moore
Journal of the American Chemical Society, 1947 , vol. 69, p. 1117,1120 Full Text Show Details
(catalytic hydrogenation);
Murakami,M. et al.
Bulletin of the Chemical Society of Japan, 1962 , vol. 35, p. 11 - 15 Full Text View citing articles Show Details
4
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Rx-ID: 455067 Find similar reactions
Blicke; Johnson
Journal of the American Pharmaceutical Association (1912-1977), 1956 , vol. 45, p. 443 Full Text View citing articles Show Details
5
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Rx-ID: 7683927 Find similar reactions
With ethanol; sodium
Chiang
Journal of the Chinese Chemical Society (Peking), 1951 , vol. 18, p. 65,69, 74 Full Text Show Details
6
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Rx-ID: 8093438 Find similar reactions
With perchloric acid; palladium; acetic acid
T=100°C; Hydrogenation;
Kindler; Hedemann; Schaerfe
Justus Liebigs Annalen der Chemie, 1948 , vol. 560, p. 215,219 Full Text Show Details
7
Synthesize Find similar Multi-step reaction with 3 steps 1: 93 percent / DEAD; Ph3P / tetrahydrofuran 2: 84 percent / N2H4 / methanol / Heating 3: 89 percent / H2 / PtO2 / acetic acid View Scheme
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Rx-ID: 12887589 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
8
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Multi-step reaction with 2 steps 1: 84 percent / N2H4 / methanol / Heating 2: 89 percent / H2 / PtO2 / acetic acid View Scheme
Rx-ID: 12895582 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
9
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Multi-step reaction with 2 steps 1: formic acid 2: aqueous HCl View Scheme
Rx-ID: 22031655 Find similar reactions
Blicke; Johnson
Journal of the American Pharmaceutical Association (1912-1977), 1956 , vol. 45, p. 443 Full Text View citing articles Show Details
10
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Multi-step reaction with 2 steps 1: palladium; acetic acid; sulfuric acid / Hydrogenation 2: palladium; acetic acid; perchloric acid / 80 - 90 °C / Hydrogenation View Scheme
Rx-ID: 22036722 Find similar reactions
Kindler; Hedemann; Schaerfe
Justus Liebigs Annalen der Chemie, 1948 , vol. 560, p. 215,219 Full Text Show Details
11
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Multi-step reaction with 2 steps 1: Gewinnung ueber das Lg-Hydrogentartrat 2: aqueous hydrochloric acid; ethanol; platinum / 50 °C / Hydrogenation View Scheme
Rx-ID: 22064422 Find similar reactions
Leithe
Chemische Berichte, 1932 , vol. 65, p. 660,665 Full Text Show Details
12
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Rx-ID: 22936312 Find similar reactions
PHARMACOPEIA, INC.
Patent: WO2004/33440 A1, 2004 ; Location in patent: Page 312 ;
23%
Title/Abstract Full Text Show Details
Schering Corporation
Patent: US2004/106794 A1, 2004 ; Location in patent: Page 173 ;
23%
Title/Abstract Full Text Show Details
13
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Rx-ID: 22936314 Find similar reactions
PHARMACOPEIA, INC.
Patent: WO2004/33440 A1, 2004 ; Location in patent: Page 312 ;
Title/Abstract Full Text Show Details
Schering Corporation
Patent: US2004/106794 A1, 2004 ; Location in patent: Page 173 ;
15%
Title/Abstract Full Text Show Details
14
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Rx-ID: 25225061 Find similar reactions
Monsanto Company
Patent: US3965220 A1, 1976 ; Title/Abstract Full Text Show Details
The following list of illustrative compounds is therefore to be read in the light of the above teachings. Aliphatic and Alicyclic Amines methylamine n-butylamine tetramethylammonium chloride ... cyclopropylamine cyclohexylamine dicyclohexylamine 1-cyclohexyl-2-aminopropane tricyclopropylamine methyl diethylamine nonyldiundecylamine ...
15
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With water; potassium hydroxide
Reflux; optical yield given as percent ee;
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Rx-ID: 32451772 Find similar reactions
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
16
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Rx-ID: 32451867 Find similar reactions
With lithium aluminium tetrahydride in diethyl ether
3 h; Inert atmosphereReflux;
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
17
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Rx-ID: 32451868 Find similar reactions
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
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 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
18
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Rx-ID: 32451869 Find similar reactions
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / 3 h / Inert atmosphere; Reflux 2: Candida antartica lipase B; triethylamine / n-heptane / 2 h / 35 °C / Inert atmosphere; Enzymatic reaction
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
3: water; potassium hydroxide / Reflux View Scheme
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 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
19
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Rx-ID: 32451899 Find similar reactions
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
20
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Rx-ID: 32451900 Find similar reactions
Multi-step reaction with 2 steps 1: Candida antartica lipase B; triethylamine / n-heptane / 2 h / 35 °C / Inert atmosphere; Enzymatic reaction 2: water; potassium hydroxide / Reflux 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
21
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Rx-ID: 32451957 Find similar reactions
Multi-step reaction with 2 steps 1: ammonium acetate / Reflux 2: lithium aluminium tetrahydride / diethyl ether / 3 h / Inert atmosphere; Reflux 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
22
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Rx-ID: 32451958 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; 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
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 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
23
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Rx-ID: 32451959 Find similar reactions
Multi-step reaction with 4 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 h / 35 °C / Inert atmosphere; Enzymatic reaction 4: water; potassium hydroxide / Reflux 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; triethylamine / n-heptane / 2 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
24
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Stage #1: With trifluoroacetic acid in dichloromethane
T=0°C; 3 h; Stage #2: With potassium hydroxide in ethyl acetate
T=0 - 25°C; Hide Experimental Procedure
Rx-ID: 32592951 Find similar reactions
RANBAXY LABORATORIES LIMITED; DAS, Biswajit; UPADHYAY, Dilip, J.; PURNAPATRE, Kedar; GHOSH, Soma; KATOCH, Rita
Patent: WO2012/14109 A1, 2012 ; Location in patent: Page/Page column 24 ; Title/Abstract Full Text Show Details
3.b: To an ice-cooled solution of compound obtained from Step a (60 g) indichloromethane (360 ml) was added trifluoroacetic acid (120 ml) and stirred for 3 hours. After completion, the solvent was evaporated and crude product so obtained was dissolved in ethyl acetate (200 ml) and cooled to 0°C. To this cooled solution was added potassium hydroxide (5N) and stirred at room temperature for 1 hour to 2 hours. The organic layer was separated and aqueous layer was extracted with ethyl acetate. The combined organic layer was stirred with 5N potassium hydroxide solution (250 ml) for 1 hour to 2 hours. The organic layer was separated and dried over anhydrous sodium sulphate and evaporated under vacuum to get brown oily compound. Yield: 90percent ( 31.6g)EIMS (m/z): 142.42 A
B
C
D
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25
Synthesize Find similar Rx-ID: 2040169 Find similar reactions
D: 58 % Chromat.
With lithium methanolate; hydrogen; [Rh(μ-Cl)(2,5-norbornadiene)]2; (+)-1,2bis(diphenylphosphino)propane in methanol; ethanol
T=60°C; P=51714.8 Torr; 16 h;
Harsy, Stephen G.
Tetrahedron, 1990 , vol. 46, # 21 p. 7403 - 7412 Title/Abstract Full Text View citing articles Show Details
D: 58 % Chromat.
With lithium methanolate; hydrogen; [Rh(μ-Cl)(2,5-norbornadiene)]2; (+)-1,2bis(diphenylphosphino)propane in ethanol
T=60°C; P=51714.8 Torr; 16 h; other catalysts; Product distributionMechanism;
Harsy, Stephen G.
Tetrahedron, 1990 , vol. 46, # 21 p. 7403 - 7412 Title/Abstract Full Text View citing articles Show Details
26
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Rx-ID: 23014216
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Schering Corporation and Pharmacopeia, Inc.
Patent: US2004/147559 A1, 2004 ; Location in patent: Page 171; 172 ;
23%
Title/Abstract Full Text Show Details
27
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Rx-ID: 23014218 Find similar reactions
Schering Corporation and Pharmacopeia, Inc.
Patent: US2004/147559 A1, 2004 ; Location in patent: Page 171; 173 ;
15%
Title/Abstract Full Text Show Details
A
B
C
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28
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Rx-ID: 32451795 Find similar reactions
A: 38%
With Candida antartica lipase B; triethylamine in n-heptane
T=35°C; 2 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