Triethylamine → HCID 178418975, compound

Participants

Reaction Steps

Methanesulfonyl chloride (1.37 g, 929 μL, 12 mmol) was added dropwise to a stirred suspension of trans (4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester (2.15 g, 10.0 mmol) in DCM (25 mL) and triethylamine (1.42 g, 1.95 mL, 14.0 mmol). After 2.5 hours saturated aqueous sodium hydrogen carbonate solution (25 mL) was added and the phases were separated. The aqueous phase was extracted with DCM (2×20 mL). The combined organic extracts were washed with brine (50 mL), dried over sodium sulfate and concentrated under vacuum to afford 3.13 g (100%) of trans methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexyl ester an off white solid. 1H NMR (400 MHz, CDCl3): δ 4.66-4.56 (m, 1H), 4.37 (br s, 1H), 3.46 (br s, 1H), 3.00 (s, 3H), 2.18-2.02 (m, 4H), 1.74-1.61 (m, 2H), 1.43 (s, 9H), 1.31-1.19 (m, 2H).

Provenance & Evidence