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

Participants

Reaction Steps

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).

Provenance & Evidence