Sodium hydride → HCID 54167690, compound

Participants

Reaction Steps

To a solution of trimethylsulfoxonium iodide (1.16 g, 5.25 mmol) in dimethylsulfoxide (10 ml) was added sodium hydride (60% dispersion in oil, 210 mg, 5.25 mmol) under 0° C., and the solution was stirred at room temperature for 10 minutes. To the resulting mixture was added a solution of 3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acrylic acid methyl ester (1.37 g, 5.09 mmol) was added dropwise under 0° C., and it was stirred for 1 hour at room temperature and for 2 hours at 50° C. After cooling to 0° C., saturated aqueous ammonium chloride was added to quench the reaction. The mixture was extracted with diethyl ether 50 ml×2), and the organic phase was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by column chromatography (n-hexane/ethyl acetate=7/1) to give 2-(1-tert-butoxycarbonyl-4-piperidyl)-(1R*,2S*)-cyclopropane-1-carboxylic acid methyl ester.

Provenance & Evidence