(2-Nitropropyl)benzene (1-Phenyl-2-nitropropane) [C9H11NO2] by Asch

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Date

45 reactions in Reaxys

2018-05-23 21h:39m:37s (UTC)

O N

1. Query

Search as: Product, As drawn, No mixtures ))

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N O

N C–

Rx-ID: 2040168 View in Reaxys 1/45 Yield

Conditions & References With 18-crown-6 ether, potassium tert-butylate in ethanol Luening, Ulrich; Schillinger, Fritz; Chemische Berichte; vol. 123; nb. 10; (1990); p. 2073 - 2075 View in Reaxys

N O

Rx-ID: 269581 View in Reaxys 2/45 Yield > 99 %

Conditions & References 4.2. General procedure for the transfer hydrogenation of conjugated nitroalkenes General procedure: A mixture of the TsEN ligand (0.0044 mmol), [RhCl2Cp*]2 (0.002 mmol), and triethylamine (11 μL, 0.08 mmol) was dissolved in1 mL methanol and heated at 70 °C for 1 h in a glass tube. After cooling down, the solvent was removed in vacuo. Nitroalkene substrate (0.4 mmol) in EtOAc (1.0 mL) and the azeotrope of formic acid/triethylamine (0.2 mL) were added in turn. The mixture was stirred at 28 °C for the corresponding time. After completion, the solution was washed with water. The aqueous layer was extracted with EtOAc (5 mL.x.3). The combined organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the crude product, which was purified by flash chromatography (PE/EtOAc) on silica gel to provide the pure reduction product. With formic acid, dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, triethylamine, N-tosylethylenediamine in ethyl acetate, Time= 0.5h, T= 28 °C , chemoselective reaction Xiang, Jing; Sun, Er-Xiao; Lian, Chun-Xia; Yuan, Wei-Cheng; Zhu, Jin; Wang, Qiwei; Deng, Jingen; Tetrahedron; vol. 68; nb. 24; (2012); p. 4609 - 4620 View in Reaxys

91 %

With benzaldehyde, 1,2-diamino-benzene in butan-1-ol, Time= 6h, Heating Chikashita, Hidenori; Morita, Yasuhiro; Itoh, Kazuyoshi; Synthetic Communications; vol. 15; nb. 6; (1985); p. 527 - 534 View in Reaxys

90 %

4.2. Typical procedure for the reduction of conjugated nitroalkenes General procedure: The mixture of nitroalkenes 1 (0.1 g, 0.67 mmol), Hantzsch ester (0.19 g, 0.74 mmol) and S-benzyl isothiouronium chloride (14 mg, 0.067 mmol) in methanol (5 ml) was stirred at 60 °C for 5-12 h. After completion of the reaction, the crude product in methanol was concentrated and added into the excess cooled CH2Cl2. The S-benzyl isothiouronium chloride was readily precipitated out, and then filtered and washed many times with CH2Cl2 to be reused. The filtrate was evaporated and the residue was purified by flash column chromatography to give the required nitroalkanes products 2. All nitroalkanes except 2j and 2p were characterized with the reported spectroscopic data. [2] and [5] With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, S-benzyl isothiouronium chloride in methanol, T= 60 °C , Inert atmosphere Nguyen, Quynh Pham Bao; Kim, Jae Nyoung; Kim, Taek Hyeon; Tetrahedron; vol. 68; nb. 32; (2012); p. 6513 - 6516 View in Reaxys

84 %

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, Time= 12h, T= 100 °C , neat (no solvent) Chauhan, Pankaj; Kaur, Kirandeep; Bala, Neeraj; Kumar, Vikas; Chimni, Swapandeep Singh; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 50; nb. 3; (2011); p. 304 - 309 View in Reaxys

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83 %

With 3,5-diethyl 1,4-dihydropyridine-3,5-dicarboxylate in water, Time= 24h, T= 100 °C , Green chemistry, chemoselective reaction He, Qi; Xu, Zhihong; Jiang, Dehong; Ai, Wensi; Shi, Ronghua; Qian, Shan; Wang, Zhouyu; RSC Advances; vol. 4; nb. 17; (2014); p. 8671 - 8674 View in Reaxys

82 %

With sodium tetrahydroborate in tetrahydrofuran, methanol, Time= 0.666667h, Ambient temperature, other conjugated nitroalkenes, Product distribution Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 - 7457 View in Reaxys

82 %

With sodium tetrahydroborate in tetrahydrofuran, methanol, Time= 0.666667h, Ambient temperature Kabalka, George W.; Laila Guindi; Varma, Rajender S.; Tetrahedron; vol. 46; nb. 21; (1990); p. 7443 - 7457 View in Reaxys Varma, Rajender S.; Kabalka, George W.; Synthetic Communications; vol. 15; nb. 2; (1985); p. 151 - 156 View in Reaxys

81 %

With borohydride supported ion exchange resin in methanol, Time= 1h, Ambient temperature Goudgaon, Naganna M.; Wadgaonkar, Prakash P.; Kabalka, George W.; Synthetic Communications; vol. 19; nb. 5and6; (1989); p. 805 - 812 View in Reaxys

70 %

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, acetic acid in benzene, Time= 15h, T= 80 °C Inoue, Yoshio; Imaizumi, Shin; Itoh, Hiromitsu; Shinya, Takao; Hashimoto, Harukichi; Miyano, Sotaro; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 3020 - 3022 View in Reaxys

51 %

With sodium tetrahydroborate in tetrahydrofuran, methanol, Time= 0.666667h, T= 20 °C Merlino, Alicia; Boiani, Mariana; Cerecetto, Hugo; Gonzalez, Mercedes; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 67; nb. 2; (2007); p. 540 - 549 View in Reaxys With palladium on activated charcoal, water, T= 35 °C , p= 25742.8Torr , Hydrogenation Patent; Comm. Solv. Corp.; US2483201; (1945) View in Reaxys With tetrahydrofuran, diethyl ether Shechter et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 4984,4985 View in Reaxys With lithium aluminium tetrahydride, diethyl ether Gilsdorf; Nord; Journal of the American Chemical Society; vol. 74; (1952); p. 1837,1841 View in Reaxys With hydrogenchloride, tin(ll) chloride in methanol, T= -5 °C Dornow,A.; Mueller,A.; Chemische Berichte; vol. 93; (1960); p. 32 - 40 View in Reaxys With formic acid, triethylamine in N,N-dimethyl-formamide Nanjo,K.; Sekija,M.; Chemical and Pharmaceutical Bulletin; vol. 27; (1979); p. 198 - 203 View in Reaxys With sodium cyanoborohydride in ethanol Hutchins,R.O. et al.; Journal of Organic Chemistry; vol. 41; nb. 20; (1976); p. 3328 - 3329 View in Reaxys

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With tri-n-butyl-tin hydride, acetic acid, 1) methylene chloride, room temp., 24h, Yield given. Multistep reaction Palomo, Claudio; Aizpurua, Jesus M.; Cossio, Fernando P.; Garcia, Jesus M.; Lopez, M. Concepcion; Oiarbide, Mikel; Journal of Organic Chemistry; vol. 55; nb. 7; (1990); p. 2070 - 2078 View in Reaxys With hydrogen fluoride dimer, tri-n-butyl-tin hydride, 1.) methylene chloride, 20-24h, room temperature; 2.) MeOH, methylene chloride, Multistep reaction Aizpurua, J. M.; Oiarbide, M.; Palomo, C.; Tetrahedron Letters; vol. 28; nb. 44; (1987); p. 5365 - 5366 View in Reaxys With silica gel, L-Selectride, 1.) THF, RT, 30 min, Yield given. Multistep reaction Varma, Rajender S.; Kabalka, George W.; Synthetic Communications; vol. 14; nb. 12; (1984); p. 1093 - 1098 View in Reaxys With wild type Salmonella typhimurium nitroreductase, Enzymatic reaction Yanto, Yanto; Hall, Melanie; Bommarius, Andreas S.; Organic and Biomolecular Chemistry; vol. 8; nb. 8; (2010); p. 1826 1832 View in Reaxys 94 %Spectr. With 2,6-dimethylpyridine, C18H9BF6*C4H8O, hydrogen in dichloromethane-d2, Time= 24h, T= -196.16 - 40 °C , p= 3000.3Torr , Inert atmosphere, Schlenk technique, Glovebox Greb, Lutz; Daniliuc, Constantin-Gabriel; Bergander, Klaus; Paradies, Jan; Angewandte Chemie - International Edition; vol. 52; nb. 22; (2013); p. 5876 - 5879; Angew. Chem.; vol. 125; nb. 22; (2013); p. 5989 - 5992,4 View in Reaxys 75 %Chromat.

With D-glucose, glucose dehydrogenase (GDH; 10U), holo-(flavin free double bond reductase from Nicotiana tabacum), nicotinamide adenine dinucleotide phosphate in aq. phosphate buffer, Time= 24h, T= 30 °C , pH= 6.4, Enzymatic reaction Mansell, David J.; Toogood, Helen S.; Waller, John; Hughes, John M.X.; Levy, Colin W.; Gardiner, John M.; Scrutton, Nigel S.; ACS Catalysis; vol. 3; nb. 3; (2013); p. 370 - 379 View in Reaxys Typical procedure for catalytic asymmetric hydrogenation General procedure: A 10mL tube equipped with a magnetic stirring bar, substrate (0.5mmol), catalyst (0.005mmol) and KOH (0.05mmol), was vacuum-pumped and flushed with argon three times. A degassed solvent (2mL) was then added and the tube was transferred to a stainless autoclave in a glove box. The autoclave was pressurized and evacuated with hydrogen three times, and finally charged with hydrogen at a pressure of 50atm. The reaction mixture was magnetically stirred at the given temperature for 24h. After cooling to room temperature, the pressure was released. The solvent was removed in vacuo and the crude product was examined by 1H NMR to determine the conversion. The pure product was obtained by flash column chromatography using ethyl acetate/petroleum ether as the eluant. With C17H33ClIrNP2, hydrogen, potassium hydoxide in methanol, Time= 24h, T= 25 °C , p= 38002.6Torr , Autoclave, Glovebox, enantioselective reaction Yang, Zehua; Wei, Xuan; Liu, Delong; Liu, Yangang; Sugiya, Masashi; Imamoto, Tsuneo; Zhang, Wanbin; Journal of Organometallic Chemistry; vol. 791; (2015); p. 41 - 45 View in Reaxys With D-glucose, glucose/glucose dehydrogenase, ene-reductase of the Old Yellow Enzyme 1, nicotinamide adenine dinucleotide phosphate in aq. phosphate buffer, dimethyl sulfoxide, T= 30 °C , pH= 7 Forchin, Maria Chiara; Crotti, Michele; Gatti, Francesco G.; Parmeggiani, Fabio; Brenna, Elisabetta; Monti, Daniela; ChemBioChem; vol. 16; nb. 11; (2015); p. 1571 - 1573 View in Reaxys

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O Br

N O

Rx-ID: 436372 View in Reaxys 3/45 Yield

Conditions & References With silver(I) nitrite, diethyl ether, unter Ausschluss von Licht Kornblum et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 5528,5529,5532,6269,6279 View in Reaxys -1 F (v4)

B FF

O N O

O N O N+

Rx-ID: 938760 View in Reaxys 4/45 Yield

Conditions & References (i) NaOEt, EtOH, (ii) /BRN= 4225599/, DMSO, Multistep reaction Katritzky,A.R. et al.; Journal of the Chemical Society, Chemical Communications; (1979); p. 602 View in Reaxys O HO

O N

Rx-ID: 1096035 View in Reaxys 5/45 Yield

Conditions & References (i) Ac2O, H2SO4, (ii) NaBH4, DMSO, Multistep reaction Bachman,G.B.; Maleski,R.J.; Journal of Organic Chemistry; vol. 37; nb. 18; (1972); p. 2810 - 2814 View in Reaxys

N O

Rx-ID: 1553460 View in Reaxys 6/45 Yield 97 %

Conditions & References With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, water, sodium formate, (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine, T= 28 °C , Inert atmosphere Tang, Yuanfu; Xiang, Jing; Cun, Linfeng; Wang, Yuqin; Zhu, Jin; Liao, Jian; Deng, Jingen; Tetrahedron Asymmetry; vol. 21; nb. 15; (2010); p. 1900 - 1905 View in Reaxys

94.1 %

With Candida albicans, medium for yeast, Time= 72h, T= 30 °C , analogous reaction with other yeasts or with bacteria (at 37 deg C), Product distribution

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Mori; Ishiyama; Akita; Suzuki; Mitsuoka; Oishi; Chemical and Pharmaceutical Bulletin; vol. 38; nb. 12; (1990); p. 3449 3451 View in Reaxys 93 %

With sodium tetrahydroborate, silica gel in chloroform, isopropyl alcohol, Time= 0.75h, T= 25 °C Sinhababu, Achintya K.; Borchardt, Ronald T.; Tetrahedron Letters; vol. 24; nb. 3; (1983); p. 227 - 230 View in Reaxys

87 %

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, silica gel in benzene, Time= 20h, T= 60 °C Nakamura, Kaoru; Fujii, Masayuki; Oka, Shinzaburo; Ohno, Atsuyoshi; Chemistry Letters; (1985); p. 523 - 526 View in Reaxys

87 %

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, silica gel in benzene, Time= 0.5h, Heating FUJI, Masayuki; Bulletin of the Chemical Society of Japan; vol. 61; nb. 11; (1988); p. 4029 - 4036 View in Reaxys

82 %

With sodium tetrahydroborate in 1,4-dioxane, ethanol, Time= 0.75h, T= 30 °C Bhattacharjya, Anup; Mukhopadhyay, Ranjan; Pakrashi, Satyesh C.; Synthesis; nb. 9; (1985); p. 886 - 887 View in Reaxys

81 %

With baker's yeast in ethanol, water, Time= 24h, T= 35 °C Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

80 %

With yeast, water in Petroleum ether, Time= 24h, Ambient temperature Bak, Radoslaw R.; McAnda, Anita F.; Smallridge, Andrew J.; Trewhella, Maurie A.; Australian Journal of Chemistry; vol. 49; nb. 11; (1996); p. 1257 - 1260 View in Reaxys

79 %

in water, Time= 120h, T= 24 °C , baker's yeast Takeshita, Mitsuhiro; Yoshida, Sachiko; Kohno, Yoichiro; Heterocycles; vol. 37; nb. 1; (1994); p. 553 - 562 View in Reaxys

77 %

With borohydride Ultra resin in methanol, Time= 2h, T= 20 °C Barth, Michael; Shah, Syed Tasadaque Ali; Rademann, Joerg; Tetrahedron; vol. 60; nb. 39; (2004); p. 8703 - 8709 View in Reaxys

70 %

With sodium cyanoborohydride, zeolite H-ZSM5 in methanol, Time= 3h, pH 6.5 Gupta, Anuradha; Haque, Azizul; Vankar, Yashwant D.; Chemical Communications; nb. 14; (1996); p. 1653 - 1654 View in Reaxys With C=C reductase from baker's yeast, NADPH, T= 35 °C Kawai, Yasushi; Hayashi, Motoko; Inaba, Yoshikazu; Saitou, Kentarou; Ohno, Atsuyoshi; Tetrahedron Letters; vol. 39; nb. 29; (1998); p. 5225 - 5228 View in Reaxys With sodium tetrahydroborate in tetrahydrofuran, methanol, T= 20 °C Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298 View in Reaxys With glucose dehydrogenase, D-glucose, xenobiotic reductase A C25G mutant, NADPH, pH= 7.5, aq. phosphate buffer Yanto, Yanto; Yu, Hua-Hsiang; Hall, Melanie; Bommarius, Andreas S.; Chemical Communications; vol. 46; nb. 46; (2010); p. 8809 - 8811 View in Reaxys

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With xenobiotic reductase B from Pseudomonas putida JLR11, NADH in dimethyl sulfoxide, Time= 24h, T= 30 °C , pH= 7.5, aq. buffer, Enzymatic reaction Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys With D-glucose, ene-reductase KYE1 from genomic DNA of Kluyveromyces lactis ATCC 8585, nicotinamide adenine dinucleotide phosphate, Time= 12h, T= 20 °C , pH= 7.5, aq. phosphate buffer, Enzymatic reaction Yanto, Yanto; Winkler, Christoph K.; Lohr, Stephanie; Hall, Melanie; Faber, Kurt; Bommarius, Andreas S.; Organic Letters; vol. 13; nb. 10; (2011); p. 2540 - 2543 View in Reaxys 92 %Chromat.

With glucose-6-phosphate dehydrogenase, D-glucose 6-phosphate, pentaerythritol tetranitrate reductase T26S mutant, NADPH in N,N-dimethyl-formamide, Time= 48h, T= 30 °C , pH= 7, aq. phosphate buffer, Enzymatic reaction Hulley, Martyn E.; Toogood, Helen S.; Fryszkowska, Anna; Mansell, David; Stephens, Gill M.; Gardiner, John M.; Scrutton, Nigel S.; ChemBioChem; vol. 11; nb. 17; (2010); p. 2433 - 2447 View in Reaxys

93 %Chromat.

With glucose-6-phosphate dehydrogenase, β-D-glucose 6-phosphate, wild type pentaerythritol tetranitrate reductase, NADPH in N,N-dimethyl-formamide, Time= 48h, T= 30 °C , phosphate buffer, Inert atmosphere, anaerobic, Enzymatic reaction, enantioselective reaction Toogood, Helen S.; Fryszkowska, Anna; Hulley, Martyn; Sakuma, Michiyo; Mansell, David; Stephens, Gill M.; Gardiner, John M.; Scrutton, Nigel S.; ChemBioChem; vol. 12; nb. 5; (2011); p. 738 - 749 View in Reaxys With sodium tetrahydroborate in 1,4-dioxane, ethanol, T= 20 °C , Cooling with ice Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys 2.5 Bioreduction of activated alkenes and product analysis General procedure: The bioreduction of various substrates was performed in 1-ml reaction system containing 100mM potassium phosphate buffer (pH 7.0), 10mM NADH, 5mM substrate, and 50μg purified Chr-OYE1 or 500μg purified Chr-OYE2. After 2min or 16-h incubation at 30°C for Chr-OYE1 and Chr-OYE2, respectively, the reactions were terminated by extraction with ethyl acetate. The organic phase was analyzed using GC or HPLC. (0013) Preparative-scale biotransformation was performed in 30-ml reaction system for substrates 4a, 6a, and 12a–17a catalyzed with Chr-OYE1. The incubation was continued for 12h. The extracted organic phase was combined and concentrated under reduced pressure. The final product was purified with column chromatography and subjected to GC or HPLC analysis, as well as NMR analysis to confirm the structure and purity. With Chr-OYE1 (old yellow enzyme from chryseobacterium sp. CA49), β-nicotinamide adenine dinucleotide, reduced form in aq. phosphate buffer, Time= 0.0333333h, T= 30 °C , pH= 7.0, Enzymatic reaction Pei, Xiao-Qiong; Xu, Meng-Yu; Wu, Zhong-Liu; Journal of Molecular Catalysis B: Enzymatic; vol. 123; (2016); p. 91 - 99 View in Reaxys

O O

N O

Rx-ID: 1986973 View in Reaxys 7/45 Yield

Conditions & References in water, Time= 48h, T= 30 °C , microbial reduction with Rhodococcus rhodochrous IFO 3338, Yield given. Yields of byproduct given. Title compound not separated from byproducts Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi; Agricultural and Biological Chemistry; vol. 49; nb. 8; (1985); p. 2331 - 2336 View in Reaxys

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in water, Time= 48h, T= 30 °C , microbial reduction with Rhodococcus rhodochrous IFO 3338, Yield given. Yields of byproduct given Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi; Agricultural and Biological Chemistry; vol. 49; nb. 8; (1985); p. 2331 - 2336 View in Reaxys -1 F (v4)

B FF

O N

N O

Na N+

Rx-ID: 2430444 View in Reaxys 8/45 Yield

Conditions & References in pentan-1-ol, dimethyl sulfoxide, T= 25 °C , Mechanism, Rate constant Katritzky, Alan R.; Chen, Jen-Luan; Marson, Charles M.; Maia, Angalamaria; Kashmiri, M. Akram; Tetrahedron; vol. 42; nb. 1; (1986); p. 101 - 108 View in Reaxys

N C–

Rx-ID: 2450824 View in Reaxys 9/45 Yield

Conditions & References

100 % Chromat.

With pyridin-1-ium in ethanol, Time= 15h, 0.11 M pyridine/0.03 M TosOH buffer Luening, Ulrich; Schillinger, Fritz; Chemische Berichte; vol. 123; nb. 10; (1990); p. 2073 - 2075 View in Reaxys

100 % Chromat.

With pyridin-1-ium in ethanol, Time= 15h, 0.11 M pyridine/0.03 M TosOH buffer; other proton sources; other sec. nitronate anions, Product distribution Luening, Ulrich; Schillinger, Fritz; Chemische Berichte; vol. 123; nb. 10; (1990); p. 2073 - 2075 View in Reaxys O N O

N O

Rx-ID: 3964422 View in Reaxys 10/45 Yield 91 %

Conditions & References With PBI in butan-1-ol, Time= 6h, Heating Chikashita, Hidenori; Nishida, Shuichi; Miyazaki, Makoto; Morita, Yasuhiro; Itoh, Kazuyoshi; Bulletin of the Chemical Society of Japan; vol. 60; nb. 2; (1987); p. 737 - 746 View in Reaxys

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H 2N

N O

Rx-ID: 4054274 View in Reaxys 11/45 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in chloroform, Heating Beckett; Jones; Journal of Pharmacy and Pharmacology; vol. 29; nb. 7; (1977); p. 416 - 421 View in Reaxys Reaction Steps: 3 1: 50 percent Spectr. / 2 eq. oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline / CH2Cl2 / 0.25 h / 0 °C 2: NaCNBH3 / methanol / pH=3 3: 2 eq. oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline / CH2Cl2 / 48 h / 0 °C With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline, sodium cyanoborohydride in methanol, dichloromethane Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

O O

H N

LiAlH4

H 2N

1-phenyl-propanone oxime

Rx-ID: 6681954 View in Reaxys 12/45 Yield

Conditions & References Product distribution Gilsdorf; Nord; Journal of the American Chemical Society; vol. 74; (1952); p. 1837,1841 View in Reaxys O N O

Rx-ID: 7183811 View in Reaxys 13/45 Yield

Conditions & References Nibbering; de Boer; Organic Mass Spectrometry; vol. 2; (1969); p. 157,161,164,169,173 View in Reaxys

silver nitrite

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Rx-ID: 7437748 View in Reaxys 14/45 Yield

Conditions & References unter Licht-Ausschluss Kornblum et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 5528,5529,5532,6269,6279 View in Reaxys O

I N

silver nitrite

O N

compound C9H10N2O3

compound C18H20N4O6

Rx-ID: 7452798 View in Reaxys 15/45 Yield

Conditions & References T= 0 °C Kornblum et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 5528,5529,5532,6269,6279 View in Reaxys O I

O N

Rx-ID: 8711263 View in Reaxys 16/45 Yield

Conditions & References

20 %, 54 %, With sodium tetrahydroborate in ethanol, Reduction 25 % Yusubov; Perederina; Kulmanakova; Filimonov; Chi, Ki-Whan; Russian Journal of Organic Chemistry; vol. 35; nb. 9; (1999); p. 1264 - 1272 View in Reaxys O

O O

N O

Rx-ID: 9178685 View in Reaxys 17/45 Yield

Conditions & References With tris(triphenylphosphine)ruthenium(II) chloride, hydrogen in dichloromethane, Time= 24h, p= 14710.2Torr , Heating Li, Yanjun; Izumi, Taeko; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 49; nb. 4; (2002); p. 505 - 508 View in Reaxys With glycerol trinitrate reductase from Agrobacterium radiobacter, NADH in dimethyl sulfoxide, Time= 24h, T= 30 °C , pH= 7.5, aq. buffer, Enzymatic reaction

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Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys O H

methylacetylene metal salt

Rx-ID: 14479344 View in Reaxys 18/45 Yield

Conditions & References Reaction Steps: 2 1: 63 percent / NH4OAc / 5 h / Heating 2: H2; RuCl2(PPh3)3 / CH2Cl2 / 24 h / 14710.2 Torr / Heating With tris(triphenylphosphine)ruthenium(II) chloride, ammonium acetate, hydrogen in dichloromethane Li, Yanjun; Izumi, Taeko; Journal of the Chinese Chemical Society (Taipei, Taiwan); vol. 49; nb. 4; (2002); p. 505 - 508 View in Reaxys O N

Rx-ID: 18278021 View in Reaxys 19/45 Yield

Conditions & References Reaction Steps: 2 1: NaCNBH3 / methanol / pH=3 2: 2 eq. oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline / CH2Cl2 / 48 h / 0 °C With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline, sodium cyanoborohydride in methanol, dichloromethane Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

O N O O S O

Rx-ID: 22132960 View in Reaxys 20/45 Yield

Conditions & References Reaction Steps: 2 1: acetone 2: diethyl ether; silver nitrite / unter Ausschluss von Licht With silver(I) nitrite, diethyl ether, acetone Kornblum et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 5528,5529,5532,6269,6279 View in Reaxys

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Rx-ID: 27925380 View in Reaxys 21/45 Yield 27.7 %

Conditions & References With bis(norbornadiene)rhodium(l)tetrafluoroborate, hydrogen, (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane in dichloromethane, Time= 24h, T= 50 °C , p= 60804.1Torr , Autoclave, Reagent/catalyst, enantioselective reaction Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys With 1,4-dihydronicotinamide adenine dinucleotide, hydrogen in phosphate buffer, 2,2,4-trimethylpentane, T= 30 °C , pH= 7.0, Title compound not separated from byproducts. Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298 View in Reaxys

O O

Rx-ID: 28714426 View in Reaxys 22/45 Yield

Conditions & References With glucose-6-phosphate, pentaerythritol tetranitrate reductase, NADP+, glucose 6-phosphate dehydrogenase in 2,2,4-trimethylpentane, sec-Butylbenzene, Time= 72h, T= 30 °C , pH= 7, aq. phosphate buffer, Inert atmosphere, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803 View in Reaxys With (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine, Rh(norbornadiene)2SbF6, hydrogen in dichloromethane, Time= 36h, T= 70 °C , p= 38002.6Torr , Autoclave, Catalytic behavior, Reagent/catalyst, Temperature, Time, Pressure, Overall yield = 92 percent; enantioselective reaction Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys

O N

N O

Rx-ID: 29629445 View in Reaxys 23/45 Yield 41 %, 10 %

Conditions & References With palladium 10 on activated carbon, hydrogen in methanol, Time= 0.666667h, T= 20 °C Durchschein, Katharina; Ferreira-Da Silva, Bianca; Wallner, Silvia; MacHeroux, Peter; Kroutil, Wolfgang; Glueck, Silvia Maria; Faber, Kurt; Green Chemistry; vol. 12; nb. 4; (2010); p. 616 - 619 View in Reaxys

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O N

Rx-ID: 32288948 View in Reaxys 24/45 Yield

Conditions & References With glucose-6-phosphate dehydrogenase, β-D-glucose 6-phosphate, wild type pentaerythritol tetranitrate reductase, NADPH in N,N-dimethyl-formamide, Time= 4h, T= 30 °C , phosphate buffer, Inert atmosphere, anaerobic, Enzymatic reaction, enantioselective reaction Toogood, Helen S.; Fryszkowska, Anna; Hulley, Martyn; Sakuma, Michiyo; Mansell, David; Stephens, Gill M.; Gardiner, John M.; Scrutton, Nigel S.; ChemBioChem; vol. 12; nb. 5; (2011); p. 738 - 749 View in Reaxys

N O

Rx-ID: 36298029 View in Reaxys 25/45 Yield

Conditions & References With glucose dehydrogenase, D-Glucose, NADPH, citric acid in aq. phosphate buffer, ethanol, Time= 10h, T= 9 °C , pH= 6, Sonication, enantioselective reaction Burda, Edyta; Reß, Tina; Winkler, Till; Giese, Carolin; Kostrov, Xenia; Huber, Tobias; Hummel, Werner; Gröger, Harald; Angewandte Chemie - International Edition; vol. 52; nb. 35; (2013); p. 9323 - 9326; Angew. Chem.; vol. 125; nb. 35; (2013); p. 9493 - 9496 View in Reaxys

H N

N O

Rx-ID: 38266826 View in Reaxys 26/45 Yield

Conditions & References Reaction Steps: 2 1: N-butylamine; acetic acid / 60 °C / Sonication 2: (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate / dichloromethane / 24 h / 50 °C / 60804.1 Torr / Autoclave With bis(norbornadiene)rhodium(l)tetrafluoroborate, hydrogen, acetic acid, N-butylamine, (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane in dichloromethane, 1: |Henry Nitro Aldol Condensation Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys O

N O

Rx-ID: 38266828 View in Reaxys 27/45 Yield

Conditions & References Reaction Steps: 2 1: N-butylamine; acetic acid / 60 °C / Sonication 2: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C / Cooling with ice With sodium tetrahydroborate, acetic acid, N-butylamine in 1,4-dioxane, ethanol, 1: |Henry Nitro Aldol Condensation

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Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys

H N

O H

N O

Rx-ID: 38266829 View in Reaxys 28/45 Yield

Conditions & References Reaction Steps: 2 1: N-butylamine; acetic acid / 60 °C / Sonication 2: (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; Rh(norbornadiene)2SbF6; hydrogen / dichloromethane / 36 h / 70 °C / 38002.6 Torr / Autoclave With (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine, Rh(norbornadiene)2SbF6, hydrogen, acetic acid, N-butylamine in dichloromethane, 1: |Henry Nitro Aldol Condensation Li, Shengkun; Huang, Kexuan; Zhang, Xumu; Chemical Communications; vol. 50; nb. 64; (2014); p. 8878 - 8881 View in Reaxys O

N O

Rx-ID: 45462129 View in Reaxys 29/45 Yield

Conditions & References With ammonium acetate, Time= 2h, Reflux Ding, Qiuping; Ye, Shengqing; Cheng, Guolin; Wang, Peng; Farmer, Marcus E.; Yu, Jin-Quan; Journal of the American Chemical Society; vol. 139; nb. 1; (2017); p. 417 - 425 View in Reaxys

N O

Rx-ID: 4814683 View in Reaxys 30/45 Yield 57 %

Conditions & References With sodium borodeuteride in dichloromethane, isopropyl alcohol McAnda, Anita F.; Roberts, Kade D.; Smallridge, Andrew J.; Ten, Abilio; Trewhella, Maurie A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 501 - 504 View in Reaxys With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, water, sodium formate, (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine, T= 28 °C , Inert atmosphere Tang, Yuanfu; Xiang, Jing; Cun, Linfeng; Wang, Yuqin; Zhu, Jin; Liao, Jian; Deng, Jingen; Tetrahedron Asymmetry; vol. 21; nb. 15; (2010); p. 1900 - 1905 View in Reaxys

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O N

Rx-ID: 4823512 View in Reaxys 31/45 Yield 73 %

Conditions & References With Mauripan Instant Dry Yeast, water in Petroleum ether, Time= 24h, Ambient temperature McAnda, Anita F.; Roberts, Kade D.; Smallridge, Andrew J.; Ten, Abilio; Trewhella, Maurie A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 501 - 504 View in Reaxys O

Rx-ID: 16989887 View in Reaxys 32/45 Yield

Conditions & References Reaction Steps: 2 1: 50 percent / cyclohexyalamine, glacial acetic acid / 6 h / 100 °C 2: Mauripan Instant Dry Yeast, D2O / light petroleum / 24 h / Ambient temperature With Mauripan Instant Dry Yeast, water-d2, cyclohexylamine, acetic acid in Petroleum ether McAnda, Anita F.; Roberts, Kade D.; Smallridge, Andrew J.; Ten, Abilio; Trewhella, Maurie A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 501 - 504 View in Reaxys O

N O

Rx-ID: 16989888 View in Reaxys 33/45 Yield

Conditions & References Reaction Steps: 2 1: 50 percent / cyclohexyalamine, glacial acetic acid / 6 h / 100 °C 2: 73 percent / Mauripan Instant Dry Yeast, H2O / light petroleum / 24 h / Ambient temperature With Mauripan Instant Dry Yeast, water, cyclohexylamine, acetic acid in Petroleum ether McAnda, Anita F.; Roberts, Kade D.; Smallridge, Andrew J.; Ten, Abilio; Trewhella, Maurie A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 501 - 504 View in Reaxys O

C-phenyl-C-<2-methoxy-naphthyl-(1)>-methylamine

Rx-ID: 16998328 View in Reaxys 34/45 Yield

Conditions & References Reaction Steps: 2 1: 62 percent / cyclohexylamine, glacial acetic acid / 6 h / 100 °C 2: 57 percent / NaBD4 / CH2Cl2; propan-2-ol With sodium borodeuteride, cyclohexylamine, acetic acid in dichloromethane, isopropyl alcohol

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McAnda, Anita F.; Roberts, Kade D.; Smallridge, Andrew J.; Ten, Abilio; Trewhella, Maurie A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 501 - 504 View in Reaxys O

O N

O 2H

Rx-ID: 29820274 View in Reaxys 35/45 Yield

Conditions & References With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer, water-d2, sodium formate, (R,R)-N-(p-toluenesulfonyl)-1,2diphenylethylenediamine, T= 28 °C , Inert atmosphere Tang, Yuanfu; Xiang, Jing; Cun, Linfeng; Wang, Yuqin; Zhu, Jin; Liao, Jian; Deng, Jingen; Tetrahedron Asymmetry; vol. 21; nb. 15; (2010); p. 1900 - 1905 View in Reaxys O 2H

Rx-ID: 4823511 View in Reaxys 36/45 Yield

Conditions & References With Mauripan Instant Dry Yeast, water-d2 in Petroleum ether, Time= 24h, Ambient temperature, Title compound not separated from byproducts McAnda, Anita F.; Roberts, Kade D.; Smallridge, Andrew J.; Ten, Abilio; Trewhella, Maurie A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 501 - 504 View in Reaxys 2H

O N O

Rx-ID: 7602006 View in Reaxys 37/45 Yield

Conditions & References C6H5CD2CH(COOH)CH3 1)Pb(OAc)4, hβ, I2 -> C6H5CD2CH(I)CH3 2)NaNO2, Harnstoff Nibbering; de Boer; Organic Mass Spectrometry; vol. 2; (1969); p. 157,161,164,169,173 View in Reaxys O

H O

Rx-ID: 16989889 View in Reaxys 38/45 Yield

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McAnda, Anita F.; Roberts, Kade D.; Smallridge, Andrew J.; Ten, Abilio; Trewhella, Maurie A.; Journal of the Chemical Society - Perkin Transactions 1; nb. 3; (1998); p. 501 - 504 View in Reaxys 2H 2H

N O

Rx-ID: 7603523 View in Reaxys 39/45 Yield

Conditions & References C6H5CH2CH(Br)CD3, NaNO2, Harnstoff, Phloroglucin Nibbering; de Boer; Organic Mass Spectrometry; vol. 2; (1969); p. 157,161,164,169,173 View in Reaxys

N O

O O

Rx-ID: 10549345 View in Reaxys 40/45 Yield 31 %

Conditions & References With 1,3-bis-(diphenylphosphino)propane, caesium carbonate, bis(1,5-cyclooctadiene)diiridium(I) dichloride in toluene, Time= 72h, T= 150 °C , Wadsworth-Emmons reaction Black, Phillip. J.; Cami-Kobeci, Gerta; Edwards, Michael G.; Slatford, Paul A.; Whittlesey, Michael K.; Williams, Jonathan M. J.; Organic and Biomolecular Chemistry; vol. 4; nb. 1; (2006); p. 116 - 125 View in Reaxys

O HO

H N

O H

N O

Rx-ID: 1986970 View in Reaxys 41/45 Yield

Conditions & References in water, Time= 48h, T= 30 °C , microbial reduction with Rhodococcus rhodochrous IFO 3338; other pH, other microoranism, Product distribution Sakai, Kunikazu; Nakazawa, Akiko; Kondo, Kiyoshi; Ohta, Hiromichi; Agricultural and Biological Chemistry; vol. 49; nb. 8; (1985); p. 2331 - 2336 View in Reaxys H

O N O

H 2N

O N O

Rx-ID: 2677945 View in Reaxys 42/45

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Yield

Conditions & References

0.52 mg, 0.13 mg, 0.011 mg

With Clostridium innocuum, M10 broth, Time= 120h, T= 37 °C Mori; Ishiyama; Akita; Suzuki; Mitsuoka; Oishi; Chemical and Pharmaceutical Bulletin; vol. 38; nb. 12; (1990); p. 3449 3451 View in Reaxys

O H N

O N O

Rx-ID: 3963683 View in Reaxys 43/45 Yield

Conditions & References With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline in dichloromethane, Time= 48h, T= 0 °C , Yield given. Yields of byproduct given Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys

O O

H 2N

N N

O N O

Rx-ID: 3984409 View in Reaxys 44/45 Yield

Conditions & References

30 % Spectr., 70 % Spectr.

With oxaziridinium tetrafluoroborate derived from N-methyl-1,2,3,4-tetrahydroisoquinoline in dichloromethane, Time= 48h, T= 0 °C Hanquet, Gilles; Lusinchi, Xavier; Tetrahedron; vol. 50; nb. 42; (1994); p. 12185 - 12200 View in Reaxys -1 F (v4)

B FF

O N

N O

N+

Rx-ID: 2430443 View in Reaxys 45/45 Yield

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