(2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

Base Information

Chemical Name:(2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate
CAS No.:1374003-51-6
Molecular Formula:C₂₁H₁₉N₃O₆
Molecular Weight:409.398
Hs Code.:

Synonyms:(2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

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Chemical Property of (2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

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Technology Process of (2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

There total 2 articles about (2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1734-79-8
3-(4-nitrophenyl)-2-propenal

: 55828-02-9
2-benzoylamino-2-cyanoacetic acid ethyl ester

: (2R,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

: (2S,3R,5S)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

: 1374003-51-6
(2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

Guidance literature:: With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; o-fluoro-benzoic acid; In methanol; at -20 ℃; for 14h; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/adsc.201100911

Reference yield:

: 3849-21-6
ethyl cyanoglyoxylate-2-oxime

: (2R,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

: (2S,3R,5S)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

: 1374003-51-6
(2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium dithionite; sodium hydrogencarbonate / water / 1 h / 35 °C

2: sodium carbonate / 0 - 20 °C

3: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; o-fluoro-benzoic acid / methanol / 14 h / -20 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; sodium dithionite; sodium hydrogencarbonate; sodium carbonate; o-fluoro-benzoic acid; In methanol; water;
DOI:10.1002/adsc.201100911

Reference yield: 66.0%

: 1374003-51-6
(2S,3S,5R)-ethyl 1-benzoyl-2-cyano-5-hydroxy-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

: 1374003-66-3
(2S,3S)-ethyl 1-benzoyl-2-cyano-3-(4-nitrophenyl)pyrrolidine-2-carboxylate

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1002/adsc.201100911