1-(hydroxymethyl)cyclohexane-1-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 1-cyanocyclohexanecarboxylate (prepared according to Fleming et. al, J. Org. Chem. 2005, 70, 2200) (8.54 g, 51.10 mmol) in anhydrous tetrahydrofuran (300 mL) was added anhydrous methanol (3.1 mL, 78.00 mmol) and lithium borohydride (4.0 M solution in tetrahydrofuran 19 mL, 76 mmol). The reaction solution was heated to reflux under a nitrogen atmosphere for 4 hours, cooled to ambient temperature. The mixture was quenched by the slow addition of saturated aqueous ammonium chloride (5 mL). The mixture was diluted with ethyl acetate (400 mL), washed with a 2:1 mixture of saturated aqueous ammonium chloride and water (2×300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as a colorless oil (6.30 g, 89%): 1H NMR (300 MHz, CDCl3) δ 3.55 (s, 2H), 2.78 (br s, 1H), 1.98-1.93 (m, 2H), 1.74-1.69 (m, 4H), 1.63-1.48 (m, 4H). The reaction solution was heated to reflux under a nitrogen atmosphere for 4 hours The mixture was quenched by the slow addition of saturated aqueous ammonium chloride (5 mL) The mixture was diluted with ethyl acetate (400 mL) washed with a 2:1 mixture of saturated aqueous ammonium chloride and water (2×300 mL) dried over anhydrous magnesium sulfate filtered concentrated in vacuo