3-(r)-t-Butyldimethylsilyloxymethyl-4-(s)-(3-fluorophenyl)pyrrolidine → 2-(R)-(3-(R)-(t-Butyldimethylsilyloxymethyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclopentyl)propanoic acid, benzyl ester
Reaction equation
O[C@@H:2]([CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[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]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[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 100 mg (0.40 mmol) of 2-(S)-hydroxy-3-(cyclopentyl)propanoic acid, benzyl ester (from EXAMPLE 20, Step G) and 154 mg (0.49 mmol) of 3-(R)-(t-butyldimethylsilyloxy-methyl)-4-(S)-(3-fluorophenyl)pyrrolidine (from EXAMPLE 20, Step H) using a procedure analogous to that described in EXAMPLE 1, Step G to provide 189 mg (87%) of the title compound: RF: 0.59 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 0.0 (s, 6H), 0.84 (s, 9H), 1.05-1.09 (m, 2H), 1.45-1.84 (m, 9H), 2.32 (m, 1H), 2.64 (br t, 1H), 2.74 (br t, 1H), 2.94 (br q, 1H), 3.04-3.15 (m, 2H), 3.37-3.57 (m, 3H), 5.16 (s, 2H), 6.83-6.98 (m, 3H), 7.16-7.39 (m, 6H).
Sources & evidence
- ORD record
- ord-dbbde3a2073642ef8fe998841cc8f176
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06265434B1
Reaction notes
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