Triethylamine → trans-[2-(Acryloyl-but-3-enyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester

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Reaction Steps

Acryloyl chloride (47 mg, 0.50 mmol) was added at 0° C. to a solution of trans-(2-but-3-enylamino-cyclohexyl)-carbamic acid tert-butyl ester (123 mg, 0.46 mmol) and triethylamine (51 mg, 0.51 mmol) in dichloromethane (3 ml), and the reaction mixture was allowed to reach room temperature over 3 h. After partitioning between dichloro-methane and 10% aq. citric acid solution, the organic layer was washed with 1 M aq. sodium carbonate solution and brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (103 mg, 70%). Light yellow solid, MS (ISP) 323.3 (M+H)+.

Provenance & Evidence