(R)-2-(tert-butoxycarbonyl)amino-2-(4-benzyloxyphenyl)ethanol → (R)-tert-butyl (2-hydroxy-1-(4-hydroxyphenyl)ethyl)carbamate

Participants

Reaction Steps

[(R)-1-(4-Benzyloxy-phenyl)-2-hydroxy-ethyl]-carbamic acid t-butyl ester (2.013 g, 5.87 mmol) and 10% Palladium on active carbon (0.300 g, 0.294 mmol) were mixed in ethanol (15 ml) and dichloromethane (5 ml). The hydrogenation was carried at 1 atmosphere at room temperature overnight. The catalyst was filtered out. The filtrate was concentrated to a white solid (1.350 g, 91% yield): 1H NMR (400 MHz, MeOD) δ ppm 7.36 (d, 2H), 6.97 (m, 2H), 3.83 (m, 1H), 3.54 (dt, J=3.2, 1.5 Hz, 2 H), 1.66 (m, 9H); LCMS (ESI) m/e 254.1 [(M+H), calcd. for C13H20NO4 254.3].

Provenance & Evidence