Nitrogen → HCID 54321703, compound

Participants

Reaction Steps

A mixture of 2,4-dihydroxy-N-formylmorphinan-6-one (3.6 g, 12 mmol), 5-chloro-1-phenyltetrazole (2.3 g, 12.7 mmol) and anhydrous K2CO3 (8.4 g, 60.8 mmol) in 150 ml DMF was stirred at 80+ 5° C. for 16 hrs uner N2. The K2CO3 was filtered off and washed with 10 ml DMF. The combined filtrates were evaporated under vacuum to afford a dark brown residue which was taken up in 200 ml 2 N NaOH and the aqueous solution washed with ether (2×100 ml). The basic solution was the acidified with conc. HCl and extracted with CHCl3 :i-PrOH=3:2. The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to give 6.3 g of a gum. The crude product was chromatographed over silica gel and eluted with CHCl3 /MeOH=40:1 to give 1.3 g of pure ketone which after crystallization from DMF-EtOAc had a m.p. of 254°-256°.

Provenance & Evidence