3-benzyloxy-2-[N-(tert-butoxycarbonyl)amino]-2-methylpropanoic acid tert-butyl ester → 2-[N-(tert-butoxycarbonyl)amino]-3-hydroxy-2-methylpropanoic acid tert-butyl ester

Participants

Reaction Steps

A suspension of the benzyl ether 8 (540 mg, 1.48 mmol) and 10% Pd—C (130 mg) in 20 mL of CH3OH was stirred under an H2 atmosphere overnight. The reaction mixture was filtered over Celite?, and the filtrate was concentrated under reduced pressure. Purification via silica gel column chromatography (30% EtOAc in hexane) provided a quantitative yield of 9 (407 mg, 100%) as a colorless solid: mp 44-45° C. (EtOAc/hexane); 1H NMR (CDCl3) 6.437 (3H, s), 1.442 (9H, s), 1.48 (9H, s), 3.72 (1H, d, J=11.2), 4.00 (1H, d, J=11.2), 5.32 (1H, broad s). Anal. (C13H25NO5) C, H, N.

Provenance & Evidence