3-(r)-t-Butyldimethylsilyloxymethyl-4-(s)-(3-fluorophenyl)pyrrolidine → 2-(r)-(3-(r)-(t-Butyldimethylsilyloxymethyl)-4-(s)-(3-fluoro-phenyl)pyrrolidin-1-yl)-3-(cyclopropyl)propanoic acid, 4-(methoxy)benzyl ester
Reaction equation
O[C@@H:2]([CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4].[Si:19]([O:26][CH2:27][C@@H:28]1[C@@H:32]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[CH2:31][NH:30][CH2:29]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[Si:19]([O:26][CH2:27][C@@H:28]1[C@@H:32]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[CH2:31][N:30]([C@H:2]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[O:4])[CH2:29]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 200 mg (0.8 mmol) of 2-(S)-hydroxy-3-cyclopropyl propanoic acid, 4-(methoxy)benzyl ester (from EXAMPLE 21, Step B) and 321 mg (1.0 mmol) of 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-(3-fluorophenyl)pyrrolidine (from EXAMPLE 20, Step H) using a procedure analogous to that described in EXAMPLE 1, Step G to provide 396 mg (91%) of the title compound: RF: 0.59 (4:1 a/v hexanes/EtOAc); 1H NMR (300 MHz) δ 0.01-0.14 (m, 81), 0.39-0.54 (m, 2H), 0.72 (m, 11H), 0-85 (s, 9H), 1.61-1.72 (m, 2H), 2.34 (m, 1H), 2.64 (br t, 1H), 2.75 (br t, 1H), 2.95-3.17 (m, 31), 3.38-3.60 (m, 3H), 3.82 (s, 3H), 5.13 (s, 3H), 6.85-7.00 (m, 5H), 7.18-7.36 (m, 3H).
Sources & evidence
- ORD record
- ord-33cef4540f3a40b1ac8061cb3925dd2c
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265434B1
Reaction notes
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