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

HRID 1068176Notes

Reaction equation

HRID 1068176 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@@:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH3:25])[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>CCCCCC.CCOC(C)=O>[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@@:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH3:25])[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

4

Reactant 2

HCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidineHCID 1317226972-(R)-(3-(S)-hydroxymethyl-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)propionic acid, benzyl ester

Product 1

HCID 1317226962-(R)-(3-(S)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl) propionic acid, benzyl ester

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared from 2-(R)-(3-(S)-hydroxymethyl-4-(S)-phenylpyrrolidin-1-yl)-2-(phenyl)propionic acid, benzyl ester (from Step B) using a procedure analogous to that described in preparation of Aldehyde 1. For the title compound: RF: 0.46 (4:1 v/v hexane/EtOAc); 1H NMR (300 MHz, CDCl3) δ1.73 (s, 3H), 2.95-3.10 (m, 3H), 3.33 (m, 1H), 3.50-3.63 (m, 2H), 5.25 (s, 2H), 7.12-7.38 (m, 15H), 9.62 (d, J=1.6 Hz).

Sources & evidence

ORD record
ord-5ed6ef86ed884bb1a41785298e1cf9a3
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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