Sodium Cyanide → HCID 178453919, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexylmethyl ester (0.93 mg, 3.00 mmol) and sodium cyanide (0.44 g, 9.00 mmol) in DMSO (10 mL) was stirred at 90° C. for 4 hours. After cooling the mixture was partitioned between ethyl acetate and brine and the aqueous phase was extracted with ethyl acetate (×2). The combined organic extracts were washed with water, brine, dried with sodium sulfate and concentrated under vacuum to give 0.72 g (100%) of trans (4-cyanomethyl-cyclohexyl)-carbamic acid tert-butyl ester as a white solid. 1H NMR (400 MHz, CDCl3) δ: 4.38 (br s, 1H), 3.45-3.33 (m, 1H), 2.26 (d, 2H), 2.10-2.02 (m, 2H), 1.96-1.87 (m, 2H), 1.71-1.57 (m, 1H), 1.45 (s, 9H), 1.26-1.03 (m, 4H).

Provenance & Evidence