Hydrochloric Acid → N-Isopropyloxycarbonyl-N-(2-allyloctanoyl)-(R)-1-phenylethylamine

Participants

Reaction Steps

To a solution of 40.0 g (0.14 mol) of (R)-N-allyl-N-octanoyl-1-phenylethylamine in 400 ml of toluene was added dropwise 105 ml (0.17 mol) of tert-butylmagnesium chloride (1.6 M) at room temperature, and the reaction was allowed to proceed at 70° C. for 6 hours. The reaction mixture was cooled to room temperature and, then, 51.0 g (0.42 mol) of isopropyl chlorocarbonate was added, and the reaction was allowed to proceed at room temperature for 15 hours. After completion of the reaction, the reaction mixture was added dropwise to 170 ml of a 1 N aqueous solution of hydrochloric acid in an ice bath. The reaction mixture was extracted with 400 ml of hexane, and the organic layer was washed with 100 ml of a saturated aqueous solution of sodium chloride and then concentrated under reduced pressure to give 52.1 g of a crude product. The crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1) to give 41.0 g of the title compound as a colorless oil (yield 78%, diastereomer ratio (1R,2S):(1R,2R)=80:20).

Provenance & Evidence