Bromomethylcyclopropane → HCID 70570835, compound

Participants

Reaction Conditions

Reaction Steps

A slurry was made by the addition of sodium bicarbonate (1.24 g, 14.8 mol) to a solution of 3,14-dimethoxy-8β-methylmorphinan-6-one hydrochloride (37) (1.3 g, 3.7 mmol) and cyclopropylmethyl bromide (1 ml, 10.7 mmol) in 25 ml of dimethylformamide. This reaction mixture was heated at 100° C. under a nitrogen atmosphere, and after 16 hours the reaction mixture was cooled, sodium bicarbonate was removed by suction filtration and the filter cake washed thoroughly with dimethylformamide. After removal of the solvent by vacuum distallation (oil bath temperature 40°-45° C.), the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous phase was extracted with two additional portions of ethyl acetate. The organic fractions were combined, dried over Na2SO4 and concentrated under reduced pressure. Purification of the crude product by chromatography on Florisil (eluted with graded methanol/chloroform) yielded 1.0 g (75% theory) of the title compound as a golden oil. The hydrochloride salt of this compound was formed by taking up a sample of the oil in diethyl ether and adding ethereal hydrogen chloride to provide a colorless solid.

Provenance & Evidence