benzyl (2S)-2-hydroxypropanoate → HCID 131722792, compound

HRID 1386674Notes

Reaction equation

HRID 1386674 reaction equation
[CH2:1]([O:8][C:9](=[O:13])[C@H:10]([CH3:12])O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:14]([O:21][CH2:22][C@@H:23]1[C@@H:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][NH:25][CH2:24]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>>[Si:14]([O:21][CH2:22][C@@H:23]1[C@@H:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][N:25]([C@H:10]([CH3:12])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:13])[CH2:24]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 11052238benzyl (2S)-2-hydroxypropanoateHCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine

Product 1

HCID 131722792HCID 131722792, compoundYield 66.3%

Procedure

The title compound was prepared from 242 mg (1.3 mmol) of (S)-lactic acid, benzyl ester (from EXAMPLE 7, Step A) and 310 mg (1.0 mmol) of 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine (from EXAMPLE 1, Step E) using a procedure analogous to that described in EXAMPLE 1, Step G to provide 301 mg (62%) of the title compound: RF: 0.47 (4:1 v/v hexanes/EtOAc). 1H NMR (300 MHz) δ 0.0 (s, 6H), 0.85 (s, 9H), 1.41 (d, J=6.0 Hz, 3H), 2.41-3.62 (m, 9H), 5.17 (s, 2H), 7.16-7.38 (m, 10H).

Sources & evidence

ORD record
ord-e4425c3c9409422891626a1b6a22a007
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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