(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine → 2-(R)-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)acetic acid, benzyl ester

HRID 1068175Notes

Reaction equation

HRID 1068175 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:4]1.[Si](OC[C@@H]1[C@@H](C2C=CC=CC=2)CNC1)(C(C)(C)C)(C)C>>[CH:2]([C@@H:3]1[C@@H:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][N:5]([C@H:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:4]1)=[O:1]

Participants

3

Reactant 2

HCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidineHCID 1317226952-(R)-(3-(R)-hydroxymethyl-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)acetic acid, benzyl ester

Product 1

HCID 1317226942-(R)-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)acetic acid, benzyl ester

Procedure

The title compound was prepared from of 2-(R)-(3-(R)-hydroxymethyl-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)acetic acid, benzyl ester (from Step B) using a procedure analogous to that described in the preparation given above of Aldehyde 1: RF: 0.69 (3:2 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ2.70-3.32 (m, 5H), 3.61 (q, J=7.4, 1H), 4.15 (s, 1H), 5.12 (s, 2H), 7.13-7.48 (m, 15H), 9.68 (d, J=1.9, 1H).

Sources & evidence

ORD record
ord-8a12c191b6b74836b20b2f9d3b47ca4a
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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