Sodium Bicarbonate → HCID 57098303, compound

Participants

Reaction Steps

A mixture of 3,14-dimethoxymorphinan-6-one hydrochloride (6b) (1.0 g, 2.96 mmol), cyclobutylmethyl bromide (0.662 g, 4.44 mmol) and NaHCO3 (1.492 g, 17.76 mmol) in 25 ml of dimethylformamide (DMF) was refluxed at an oil bath temperature of 110° under nitrogen for 16 hours. The mixture was filtered and the residue washed with DMF whereupon the filtrate was distilled under reduced pressure (oil bath temperature 30°-40° C.) and the residual material was taken up in methylene chloride (50 ml) and water (50 ml). The two layers were separated and the aqueous layer re-extracted with methylene chloride (2×50 ml). The organic layers were combined, washed with water (20 ml), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting solid was chromatographed on Florisil, and eluted with graded methanol/chloroform mixtures to give 17-cyclobutylmethyl-3,14-dimethoxymorphinan-6-one as a yellow oil. This material was converted to its HCl salt (7) by treatment with ethereal hydrogen chloride to give 0.507 g of a light-colored solid (42% theory), m.p. 230° C. (decomposed).

Provenance & Evidence