[(R)-1-Hydroxymethyl-3-(4-hydroxy-3-nitro-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester → [(R)-3-(3-Amino-4-hydroxy-phenyl)-1-hydroxymethyl-1-methyl-propyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

An argon purged solution of [(R)-1-Hydroxymethyl-3-(4-hydroxy-3-nitro-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (3.02 g, 8.87 mmol) in ethanol (40 ml) was treated with 10% Pd on activated charcoal (0.5 g). Argon was replaced by hydrogen and the reaction was allowed to proceed under atmospheric pressure for 2 hours. The reaction suspension was filtered and the filtrate evaporated to dryness in vacuum. Silica gel chromatography (eluent: DCM/methanol 20/1 to 10/1) followed by crystallization from diethyl ether provided the title compound as colorless crystals. mp 122.1/123.0° C.

Provenance & Evidence