2-Butene, 1-bromo-3-methyl- → (-)-1-[17-(3-Methyl-2-butenyl)morphinan-3-yl]ethanone

Participants

Reaction Steps

To a mixture of 1.8 g of (-)-1-(morphinan-3-yl)ethanone, 0.6 g of sodium bicarbonate and 25 ml of dimethylformamide, was added 1.0 g of dimethylallyl bromide. After the mixture had been heated at 50° for 16 hours, it was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between 50 ml of methylene chloride and 30 ml of water. The methylene chloride solution was washed with water and dried over magnesium sulfate. Removal of the solvent gave 2.1 g (93%) of crude (-)-1-[17-(3-methyl-2-butenyl)morphinan-3-yl]ethanone. For analysis, a sample of this compound was distilled, bp 185°-195° (0.05 mm), [α]25D-76.53° (c 0.98, MeOH).

Provenance & Evidence