Acrylonitrile → (-)-3-Acetyl-17-morphinanpropanenitrile

Participants

Reaction Steps

To a mixture of 1.5 g of (-)-1-(morphinan-3-yl)ethanone, 2.3 g of triethylamine and 35 ml of absolute ethanol, was added 0.35 g of acrylonitrile. After the mixture had been heated at reflux for 16 hours the solvent and excess of reagents were removed under reduced pressure to give 1.7 g (94%) of crude (-)-3-acetyl-17-morphinanpropanenitrile. For analysis, a sample of this compound was distilled, bp 220°-230° (0.05 mm), [α]25D-65.5° (c 1.03, MeOH).

Provenance & Evidence