tert-Butyl 4(S)-(2(S)-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate → tert-Butyl 4(S)-(2(S)-hydroxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate
Reaction equation
C([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])C1C=CC=CC=1>O1CCCC1.[Pd]>[OH:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3.58 g of tert-butyl 4(S)-(2(S)-benzyloxymethyl-3-methylbutyl)-2,2-dimethyl-oxazolidine-3-carboxylate in 100 ml of tetrahydrofuran is hydrogenated at room temperature in the presence of 0.720 g of 10% Pd/C over 1 hour. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a yellowish oil. Rf=0.28 (1:2 EtOAc-heptane); Rt=4.48 (gradient I).