The general procedure for the synthesis of Cbz-1-aminocyclopropanemethanol from 1-Cbz-aminocyclopropanecarboxylic acid was as follows: to a solution of 1-[(benzyloxy)carbonyl]aminocyclopropanecarboxylic acid (0.35 g, 0.0015 mol) and triethylamine (0.25 mL, 0.0018 mol) in tetrahydrofuran (THF, 5.0 mL) was slowly added, at -10°C, of ethyl chloroformate (0.17 mL, 0.0018 mol). The reaction mixture was stirred at 0 °C for 30 min before being filtered and the solid was washed with THF. Subsequently, a solution of sodium tetrahydroborate (0.11 g, 0.0030 mol) in water (1.0 mL) was added to the filtrate at 0 °C and the mixture was stirred for 2 h at room temperature. Upon completion of the reaction, the reaction mixture was carefully quenched with 1N HCl and extracted with ethyl acetate (EtOAc). The organic phase was washed sequentially with saturated sodium bicarbonate (NaHCO3) solution and brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated to give the crude product (0.32 g, 97% yield). Liquid chromatography-mass spectrometry (LCMS) analysis showed (M + H)+ = 222.0 and (M + Na)+ = 244.0.
