Methanol → tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

Participants

Reaction Steps

A potassium carbonate powder (6.43 g) was added to a solution mixture of methanol (90 mL) and THF (10 mL) of 4-nitrobenzoic acid (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl ester (7.03 g). The resulting reaction solution was stirred at room temperature for 1 hr, and ethyl acetate and water were added thereto. The organic layer was separated, washed with saturated saline twice, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue, diethylether was added. The insoluble matter was removed by filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1) to give 4.49 g of the title compound. The physical property values of this compound were as follows:

Provenance & Evidence