Hydrochloric Acid → n-[(r)-2-Allyloctanoyl]-1-phenylethylamine

Participants

Reaction Steps

To a solution of 24.0 g (83.0 mmol) of (R)-N-allyl-N-octanoyl-1-phenylethylamine in 240 ml of toluene was added dropwise 61.5 ml (98.0 mmol) of tert-butylmagnesium chloride (1.6 M) at room temperature and, after completion of the addition, the reaction was allowed to proceed at 70° C. for 6 hours. After completion of the reaction, the reaction mixture was added dropwise to 240 ml of 1 N aqueous hydrochloric acid on an ice bath. The resulting mixture was extracted with 300 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 25.0 g of a crude product. The crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1) to give 13.1 g (76%, (1R,2S):(1R,2R)=80:20) of N-[(R)-2-allyloctanoyl]-1-phenylethylamine.

Provenance & Evidence