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

Participants

Reaction Steps

Potassium carbonate powder (6.43 g) was added to a mixed solution of (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl 4-nitrobenzoate (7.03 g) in methanol (90 ml)-THF (10 ml), and the reaction solution was stirred at room temperature for one hour. Ethyl acetate was added to the reaction solution, which was then sequentially washed with water and brine (twice). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diethyl ether was added to the resulting residue, and the insoluble matter was removed by filtration. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1) to obtain 4.49 g of the title compound.

Provenance & Evidence