反应详情

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.

1. additionafter completion of the addition
2. customAfter completion of the reaction
3. extractionThe resulting mixture was extracted with 300 ml of hexane
4. washthe organic layer was washed with 100 ml of a saturated aqueous solution of sodium chloride
5. concentrationconcentrated under reduced pressure
6. customto give 25.0 g of a crude product
7. customThe crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1)