Ethyl Acetate → HCID 66661149, compound

Participants

Reaction Steps

To a solution of 2.00 g (6.79 mmol) of tert-butyl 4-(cyanoethoxycarbonylmethylene)piperidine-1-carboxylate (WO 2006/001 752) in 33 mL of tetrahydrofuran are added dropwise, at −5° C. under argon, 4.53 mL (13.59 mmol) of a 3M solution of ethylmagnesium bromide in ether. The reaction medium is then stirred at room temperature for 12 hours. Ethyl acetate is added and the medium is cooled in a bath of ice/water, followed by addition of saturated ammonium chloride solution. The aqueous phase is separated out and extracted three times with ethyl acetate, the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel, eluting with a 95/5 mixture of cyclohexane and ethyl acetate to give 1.63 g of pure product in the form of a white powder.

Provenance & Evidence