Ethyl Acetate → HCID 66660781, compound

Participants

Reaction Steps

To a solution of 5.00 g (56.75 mmol) of ethyl acetate in 140 mL of diethyl ether are added slowly, at −78° C. under argon, 28.38 mL (56.75 mmol) of a solution of lithium diisopropylamide (2N). After stirring for 30 minutes, 12.57 g (53.91 mmol) of benzyl 4-oxopiperidine-1-carboxylate dissolved in 140 mL of diethyl ether are added dropwise, at −78° C. under argon. The reaction medium is then stirred at room temperature for 2 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 an 85/15 mixture of cyclohexane and ethyl acetate to give 13.00 g of pure product in the form of an oil.

Provenance & Evidence