(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine → HCID 131722798, compound

HRID 1386680Notes

Reaction equation

HRID 1386680 reaction equation
O[CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:9].[Si:20]([O:27][CH2:28][C@@H:29]1[C@@H:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][NH:31][CH2:30]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>>[Si:20]([O:27][CH2:28][C@@H:29]1[C@@H:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][N:31]([CH:7]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:2]2)[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[O:9])[CH2:30]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidineHCID 76477614HCID 76477614, compound

Product 1

HCID 131722798HCID 131722798, compound

Procedure

The title compound was prepared from 233 mg (0.88 mol) of (R/S)-2-hydroxy-cyclopentylacetic acid, 4-(methoxy)benzyl ester (from EXAMPLE 15, Step B) and 209 mg (0.71 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 326 mg (84%) of the title compounds as a mixture of diastereomers: RF: 0.64 (4:1 v/v hexanes/EtOAc); 1H NMR (300 Hz) δ 0.0 (2 s, 6H), 0.84, 0.85 (2 s, 9H), 1.18 (m, 11H), 1.42-1.82 (m, 7H), 2.23-2.34 (m, 2H), 2.65-3.18 (m, 6H), 3.43-3.59 (m, 2H), 3.81 (s, 3H), 5.01-5.19 (m, 2H), 6.85-6.91 (m, 2H), 7.14-7.36 (m, 7H).

Sources & evidence

ORD record
ord-5e2bd646a0d04d81961600446c9d1094
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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