Hydrochloric Acid → N-Ethyloxycarbonyl-N-(2-allyloctanoyl)-(R)-1-(3-methoxyphenyl)ethylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 0.40 g (1.3 mmol) of N-(2-allyloctanoyl)-(R)-1-(3-methoxyphenyl)ethylamine (diastereomer ratio (1R,2S):(1R,2R)=77:23) in 2 ml of DMF was added to a solution of 151 mg (3.8 mmol) of sodium hydride in 2 ml of DMF at room temperature, and the reaction was allowed to proceed at 50° C. for 1 hour. To the reaction mixture was added 0.48 ml (5.0 mmol) of ethyl chlorocarbonate, and the mixture was stirred at 50° C. for 12 hours. The reaction mixture was added dropwise to a mixed solution composed of 5 ml of a 1 N aqueous solution of hydrochloric acid and 5 ml of hexane with ice cooling, and the resulting mixture was extracted with two 20-ml portions of hexane. The organic layer was washed with 5 ml of a saturated aqueous solution of sodium chloride and concentrated under reduced pressure to give 0.49 g of a crude product. The crude product was purified on a silica gel column (ethyl acetate:hexane=20:1) to give 0.224 g of the title compound as a colorless oil (yield 46%, (1R,2S):(1R,2R)=77:23).

Provenance & Evidence