Hydrochloric Acid → HCID 70568426, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,14-dimethoxy-8α-methylmorphinan-6-one hydrochloride (26) (0.24 g, 0.68 mmol), sodium bicarbonate (0.6 g, 7.14 mmol), (+) tetrahydrofurfuryl bromide (0.4 g, 2.42 mmol) and dimethylformamide (15 ml) was heated at 110° C. for 16 hours with stirring under a nitrogen atmosphere. The mixture was filtered hot and the residue washed with 10 milliliters of dimethylformamide. Most of the DMF was removed by distillation under high vacuum (bath temperature 35° C.) and the resulting brownish material was treated with CHCl3 (50 ml) and water (25 ml). After separation of the two layers, the aqueous layer was saturated with sodium chloride and re-extracted with ethyl acetate (3×25 ml). The organic extracts were combined, dried (MgSO4) and filtered. The filtrate was concentrated to an oily solid which was chromatographed over silica gel to give a mixture of R and S isomers of the product; yield 0.181 g (66.5% theory). A portion of the free base was converted to the HCl salt by treatment with ethereal HCl to form the title compound as a tan solid.

Provenance & Evidence