Benzyl chloroformate → HCID 57585944, compound

Participants

Reaction Steps

To a solution of (3,3-dimethylcyclohexyl)amine hydrochloride (10.0 g, 0.060 mol) and N,N-diisopropylethylamine (15.8 g, 0.12 mol) in acetonitrile (125 mL) at ice bath temperature was added a solution of benzyl chloroformate (11.4 g, 0.067 mol) in acetonitrile (25 mL), dropwise. The mixture was stirred overnight, gradually warming to ambient temperature, and concentrated in vacuo. The residue was partitioned between ethyl acetate/5% citric acid solution and the layers were separated. The organic layer was washed with brine, dried over Na2SO4, adsorbed onto silica gel and purified by flash chromatography (CH2Cl2/hexanes) affording the title compound as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm: 0.85 (s, 6H), 0.92-1.02 (m, 3 H), 1.25 (d, 1 H), 1.36-1.52 (m, 3 H), 1.76 (br. d, 1 H), 3.36-3.44 (m, 1 H), 4.96 (s, 2H), 7.10 (d, 1 H), 7.27-7.36 (m, 5H).

Provenance & Evidence