Sodium Hydroxide → 1-Benzyl-cis-3-t-butoxycarbonylamino-4-methylpyrrolidine

반응식

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][CH:17]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:16]([CH3:27])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>CCOCC>[CH2:7]([N:14]1[CH2:15][C@H:16]([CH3:27])[C@H:17]([NH:19][C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:18]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

실험 절차

To a suspension of lithium aluminum hydride (3.61 g) in absolute ether (150 ml) was added dropwise a solution of 1-benzyl-4-t-butoxycarbonylamino-3-methyl-2-oxopyrrolidine (14.46 g) in absolute ether (100 ml) with stirring for an hour at -5°~3° C. After stirring for an hour at 0° C., the reaction mixture as poured into ice-water and added 50% aqueous sodium hydroxide solution, the organic layer was separated, washed with water and saturated aqueous sodium chloride successively, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from acetonitrile to give the title compound (4.87 g) as colorless prisms, mp 134°-140° C.