Potassium Carbonate → HCID 13145938, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.2 g (7.66 mmol) 4,14-dihydroxy-4-methoxy-N-methylmorphinan-6-one in 50 ml dry DMF were added 2.12 g (15.34 mmol) anhydrous K2CO3 and 3.96 g (23.07 mmol) phenyltrimethylammonium chloride and this mixture was stirred at 90° C. (bath temperature) for 4 h. After cooling to room temperature, the mixture was filtered, washed with CHCl3 and evaporated (90° C. bath temperature). The residue was partitioned between ethyl acetate and water, the organic layer separated and washed with water, dried and evaporated to give 2.1 g of a crystalline residue. After recrystallization with ethanol 1.78 g (77%) of 14-hydroxy-4-methoxy-N-methylmorphinan-6-one, m.p. 191°-193°, [α]D26 --83.9° (C 0.88, CHCl3) were obtained.

Provenance & Evidence