Potassium Carbonate → HCID 22823462, compound

Participants

Reaction Steps

A mixture of 1.57 g (5.79 mmol) 4-hydroxy-N-methylmorphinan-6-one, 1.57 g (11.36 mmol) dry K2CO3 and 1.15 g (6.37 mml) 5-chloro-1-phenyl-1H-tetrazole din 30 ml dry DMF was stirred under argon for 24 h at room temperature. Then the reaction mixture was filtered, washed with CHCl3 and the filtrate was evaporated in vacuo (70° bath temperature). The oily residue was dissolved in CHCl3 and extracted with 2×20 ml 5% tartaric acid. The aqueous layer was rendered alkaline with conc. NaOH and extracted with CHcl3. The organic layer was washed with brine, dried and evaporated to give 2.2 g of an oil, which was crystallized with EtOAc/Et2O to yield 2.05 g (85%) of N-methyl-4-(1-phenyl-1H-5-tetrazolyloxy) morphinen-6-one, m.p. 172°-174°, [α]D26 -37.4° (c 1.35, CHCl3).

Provenance & Evidence