Cyanogen Bromide → HCID 86737778, compound

Participants

Reaction Steps

4,5α-Epoxy-8α-ethyl-3-methoxy-17-methylmorphinan-6-one 3 (6.50 g, 19.8 mmole) was dissolved in chloroform (100 ml). After the addition of K2CO3 (4.12 g, 29.8 mmole), the stirred suspension was treated dropwise with a solution of cyanogen bromide (2.50 g, 23.8 mmole) in 50 ml of chloroform. After the addition was complete, the mixture was heated to reflux and refluxed for 2 hours. Cooling was followed by removal of the insoluble material by filtration. The filtrate was evaporated to a residue which crystallized on coevaporation with ethanol. The crystals were suspended in hot ethanol, the mixture cooled and the crystals collected to give 6.30 g (94%) of 5 as white needles, mp 212°-217°, in two crops.

Provenance & Evidence