Chloroform → HCID 70569626, compound

Participants

Reaction Steps

A solution of 17-cyclopropylmethyl-3,14-dimethoxy -8α-methylmorphinan-6-one (30) (0.323 g, 0.874 mmol) in chloroform (5 ml) was slowly added over a 2 to 3 minute period to a solution of boron tribromide (1.266 g, 5.053 mmol) in chloroform. A tan colored precipitate formed, and the mixture was stirred for an additional 20 minutes. The mixture was then poured carefully into a mixture of ice (8 g) and ammonium hydroxide (4 ml). After stirring the mixture at 0° to 5° C. for 40 minutes, the layers were separated and the aqueous layer was extracted with chloroform (2×20 ml). The organic extracts were combined, washed with water, dried over NaSO4, filtered and concentrated under reduced pressure to give a gummy solid. The product was purified by column chromatography on silica gel using graded methanol/chloroform mixtures as eluant. Upon removal of the solvent a gum was obtained which was dissolved in a small volume of methanol whereupon dry diethyl ether was added and insoluble material was removed by filtration. To the clear solution was added a saturated solution of HCl in ether and the salt precipitated. The precipitated solid was separated by decantantion and dissolved in a small volume of methanol. Addition of dry diethyl ether to this methanolic solution gave pure 17-cyclopropylmethyl-3-hydroxy-14-methoxy-8α-methylmorphinan-6-one hydrochloride (31) as a cream colored solid (0.064 g, 19% theory).

Provenance & Evidence