Benzyl (2S)-hydroxy(phenyl)acetate → 2-(R/S)-(3-(S)-(t-Butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)acetic acid, benzyl ester

HRID 1068174Notes

Reaction equation

HRID 1068174 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][NH:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:21]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:30])[C@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)O>>[Si:1]([O:8][CH2:9][C@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][N:12]([CH:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 667423Benzyl (2S)-hydroxy(phenyl)acetateHCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine2×

Product 1

HCID 1317226932-(R/S)-(3-(S)-(t-Butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)acetic acid, benzyl ester

Procedure

The title compound was prepared from 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenyl pyrrolidine (prepared above as Pyrrolidine 1) and (S)-mandelic acid, benzyl ester using a procedure analogous to that described in the preparation given above of Aldehyde 1. The title compound was obtained as a mixture of diastereomers: RF: 0.68 (4:1 v/v hexanes/EtOAc).

Sources & evidence

ORD record
ord-98241611234b4ce492271f2504dec204
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

Loading…