(2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate

Base Information

Chemical Name:(2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate
CAS No.:1335040-07-7
Molecular Formula:C₂₃H₂₆N₂O₃
Molecular Weight:378.471
Hs Code.:

Synonyms:(2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate

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Chemical Property of (2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate

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Technology Process of (2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate

There total 7 articles about (2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-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: 90.0%

: 1335040-05-5
(2S,3S,4R,5S)-tert-butyl 2-cyano-4-formyl-3,5-diphenylpyrrolidine-2-carboxylate

: 1335040-07-7
(2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.25h;
DOI:10.1002/anie.201310216

Reference yield:

: 68970-51-4
tert-butyl 2-amino-2-cyanoacetate

: 1335040-07-7
(2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: (S)-2-(diphenyl((triethylsilyl)oxy)methyl)pyrrolidine; 2-cyano-2-(hydroxyimino)acetic acid methylester / tetrahydrofuran / 2 h / 20 °C

1.2: 5 h / 4 °C

2.1: sodium cyanoborohydride; acetic acid / methanol / 2 h

With (S)-2-(diphenyl((triethylsilyl)oxy)methyl)pyrrolidine; 2-cyano-2-(hydroxyimino)acetic acid methylester; sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol;
DOI:10.1002/anie.201101966

Reference yield:

: 100-52-7
benzaldehyde

: 1335040-07-7
(2S,3S,4R,5S)-tert-butyl 2-cyano-4-(hydroxymethyl)-3,5-diphenylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: (S)-2-(diphenyl((triethylsilyl)oxy)methyl)pyrrolidine; 2-cyano-2-(hydroxyimino)acetic acid methylester / tetrahydrofuran / 2 h / 20 °C

1.2: 5 h / 4 °C

2.1: sodium cyanoborohydride; acetic acid / methanol / 2 h

With (S)-2-(diphenyl((triethylsilyl)oxy)methyl)pyrrolidine; 2-cyano-2-(hydroxyimino)acetic acid methylester; sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol;
DOI:10.1002/anie.201101966