Potassium Carbonate → Benzyl (1-(hydroxymethyl)cyclopropyl)carbamate

Participants

Reaction Steps

To a solution of 1-(benzyloxycarbonylamino)cyclopropanecarboxylic acid (500 mg, 2.1 mmol) in tetrahydrofuran (5 mL) at 0° C. was added B2H6. THF (1M, 2.1 mL, 2.1 mmol). The mixture was stirred at ambient temperature overnight, treated with K2CO3 (1.0 g in 5 mL H2O) and extracted with methylene chloride (3×10 mL). The organic layer was washed with brine (10 mL) and dried over Na2SO4. After evaporating the solvent, the residue was by chromatography (1:1 ethyl acetate:hexane) to give the title compound as a white solid (200 mg, 43%). 1H-NMR (300 MHz, CDCl3) δ 7.35 (m, 5H), 5.30 (br s, 1H), 5.10 (s, 2H), 3.61 (s, 2H), 3.02 (br s, 1H), 0.86 (s, 4H).

Provenance & Evidence