Cyanogen Bromide → HCID 86737787, compound

Participants

Reaction Steps

To a solution of 3,14-dimethoxy-8α,17-dimethylmorphinan-6-one (24) (0.1 g, 0.303 mmol) in methylene chloride (3 ml) was added anhydrous potassium carbonate (0.23 g) followed by cyanogen bromide (0.2 g). The mixture was refluxed overnight under a nitrogen atmosphere with stirring. After cooling, the solution was filtered and the residue washed with excess methylene chloride. The filtrate was concentrated under reduced pressure to give 0.103 g (99% theory) of 17-cyano-3,14-dimethoxy-8α-methylmorphinan-6-one (25) as a foamy solid. Examination by thin layer chromatography showed a single spot (silica gel plates; solvent system CHCl3 :MeOH, 90:10). The product was used in the next reaction without purification.

Provenance & Evidence