Lithium borohydride → Benzyl (1-(hydroxymethyl)cyclopropyl)carbamate

Participants

Reaction Steps

To a stirred solution of ethyl 1-(benzyloxycarbonylamino)cyclopropanecarboxylate (8.7 g, 33.0 mmol) in 50 mL of THF was slowly added at room temperature LiBH4 (2.26 g, 103.76 mmol) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was cooled to 0° C. and quenched by adding a 50% HOAc solution (10 mL). The reaction mixture was partitioned between 70 mL of water and 70 mL of diethyl ether. The organic phase was washed with saturated aqueous NaHCO3 solution (15 mL), brine (10 mL) and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was evaporated at 40° C. under reduced pressure to give a crude product, which was purified by column chromatography (silica gel, 200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (1:1, v/v) to give benzyl 1-(hydroxymethyl)cyclopropylcarbamate (6.36 g, 87.1%) as a white solid. MS: (M+H)+=222.1; 1H NMR (300 MHz, CDCl3): δ 7.46-7.35 (m, 5H), 5.38 (brs, 1H), 5.19 (s, 2H), 3.71 (s, 2H), 0.96 (s, 4H).

Provenance & Evidence