(2R, 3S)-N-[(tert-Butyloxy)carbonyl]-3-amino-4-phenyl-2-(triisopropylsilyloxy) butan-1-ol → (2R 3S)-N-[(tert-butyloxy)carbonyl]-3-amino-2-(triisopropylsilyloxy)-4-cyclohexyl-1-butanol

Participants

Reaction Steps

The alcohol of Step 2 (12.8 g, 29.3 mmol) was dissolved in MeOH (135 mL) and hydrogenated with 5% Rh/C at 60 psi and 60° C. for 30 hours. The filtrate was concentrated and purified by medium pressure column chromatography (silica gel, 15% ethyl acetate in hexane) to give the title compound as a white solid (8.70 g, 67% yield, mp 61°-63° C.). Anal. calcd. for C24H49NO4Si: C, 64.96; H, 11.13; N, 3.16. Found: C, 65.16; H, 11.26; N, 3.12.

Provenance & Evidence