[OH-].[Li+].C[O:4][C:5]([C@H:7]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)[CH2:10][N:9]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:8]1)=[O:6].CO.O1CCCC1>O>[C:22]([O:21][C:19]([N:9]1[CH2:10][C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)[C@H:7]([C:5]([OH:6])=[O:4])[CH2:8]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]Add lithium hydroxide (0.50 g, 12 mmol) to a solution of trans-4-(3-bromo-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (0.80 g, 2.08 mmol) in a 1:2:1 mixture of MeOH:tetrahydrofuran:water (8 mL). Stir the mixture at room temperature for 3 h then concentrate under reduced pressure to remove volatile organics. Wash the concentrated aqueous mixture with EtOAc and then acidify to pH 5 using a 0.5 M solution of citric acid. Extract the mixture with EtOAc, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to provide 0.53 g of trans-4-(3-bromo-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester.
Wird geladen…
