2,2,2-Trichloroethyl chloroformate → (-)-3-Acetylmorphinan-17-carboxylic acid (trichloroethyl)ester

Participants

Reaction Steps

To a mixture of 2.7 g of (-)-3-acetyl-N-methylmorphinan, 50 ml of benzene and 20 mg of potassium carbonate, was added dropwise 2.11 g of 2,2,2-trichloroethyl chloroformate in 10 ml of benzene. The reaction mixture was stirred at reflux temperature for 48 hours and after cooling it was diluted with 100 ml ether. The ether solution was extracted with 1 N hydrochloric acid (2×30 ml) and dried over magnesium sulfate. Removal of the solvent gave 2.8 g (66%) of crude (-)-3-acetylmorphinan-17-carboxylic acid (trichloroethyl)ester. For analysis, a sample of this compound was distilled, bp 230°-240° (0.1 mm), [α]25D-127.21° (c 1.11, MeOH).

Provenance & Evidence