Methanol → 6-Methyloximino-17-allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan

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Reaction Steps

A solution of naloxone hydrochloride (1.09 g, 3 mmol) and O-methylhydroxylamine hydrochloride (0.33 g, 3.9 mmol) in 15 mL MeOH was stirred overnight. After the addition of 3.2 mL of 10% aqueous NaOH, the mixture was refluxed for 5 h. It was cooled, diluted with approx. 100 mL of water, and extracted with 150 mL CHCl3 (3×50 mL). The combined extracts were dried (MgSO4) and evaporated. The residue obtained was recrystallized from hexane-petroleum ether. Yield 0.8 g, (75%) mp 128°-129° C. IR (KBr): No C=O absorption at 1717 cm-1. 1H NMR (CDCl3): δ 4.95 (s, C5H), 3.82 (s, OCH3). Rf: silica gel 60 in EtOAc--EtOH--NH4OH (100:1:1) 0.50. Anal. Calcd for C20H24N2O4C, 67.40; H, 6.79; N, 7.86. Found: C, 67.27; H, 6.84; N, 7.82.

Provenance & Evidence