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

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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). This reaction solution was stirred at room temperature for 1 hr. Then, ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The obtained organic layer was 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 obtained 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:

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