Water → 6-Oximino-17-allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan

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Reaction Steps

A mixture of naloxone hydrochloride (1.085 g, 3 mmol) and hydroxylamine hydrochloride (0.28 g, 4 mmol) was taken up in 30 mL of MeOH containing 2.8 mL of 10% aqueous NaOH. The mixture was stirred at room temperature for 24 h. Water was added (100 mL), and the oxime extracted into CHCl3 (3×50 mL). The extract was dried (MgSO4), and the solvent evaporated. The residue obtained was recrystallized from CH2Cl2 -petroleum ether. Yield: 840 mg (81.8%); mp: 119 C. IR: (KBr): No C=O absorption at 1717 cm-1. 1H NMR (CDCl3) δ 4.98 (s,C5H); Rf: silica gel 60 in EtOAc--EtOH--NH4OH (100:1:1) 0.13. Anal. Calcd for: C19H22N2O4C, 66.65; H, 6.48; N, 8.18. Found: C, 66.70; H, 6.52; N, 8.08.

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