The general procedure for the synthesis of 1-(hydroxymethyl)cyclopropanecarbonitrile from ethyl 1-cyanocyclopropanecarboxylate was as follows: LiBH4 (573 mg, 26.3 mmol, 2 equiv.) was added to a solution of 1-cyanocyclopropanecarboxylic acid ethyl ester (1.7 mL, 13.15 mmol, 1 equiv.) in tetrahydrofuran (THF, 18 mL). The reaction mixture was heated to 50 °C and kept at this temperature for 18 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and saturated aqueous NaHCO3 solution was slowly added until gas escape ceased. Subsequently, the reaction mixture was diluted with brine (20 mL) and extracted sequentially with ethyl acetate (EtOAc, 1 × 60 mL), dichloromethane (DCM, 3 × 60 mL) and 10% methanol/DCM solution (2 × 60 mL). All organic extracts were combined, dried with anhydrous magnesium sulfate (MgSO4), and concentrated under reduced pressure to remove the solvent, to afford 1-(hydroxymethyl)cyclopropanecarbonitrile as a clear oil (820 mg, 65% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 0.96-1.01 (2H, m), 1.27-1.31 (2H, m), 3.64 (2H, s).
