Tetrabutylammonium Fluoride → (2R,4R)-N-Boc-4-hydroxy-2-methylpyrrolidine
Reaction equation
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH3:21])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]([OH:8])[CH2:10][C@H:11]1[CH3:21])=[O:15])([CH3:20])([CH3:18])[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2R,4R)-4-(tert-butyldimethylsilyloxy)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine (3.9 g) and tetrabutylammonium fluoride (1 Mol-tetrahydrofuran solution, 12.4 ml) in tetrahydrofuran (40 ml) was stirred at 0° C. for one hour. The reaction mixture was extracted with ethyl acetate, the organic layer was separated, washed with brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (200 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give (2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine (1.96 g).