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

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Reaction Steps

A solution of oxymorphone (1.2 g, 4 mmol) and hydroxylamine hydrochloride (0.35 g, 5 mmol) in 20 mL of methanol was treated with 2 mL of 10% aqueous NaOH and stirred at room temperature for 15 h. The reaction mixture was poured into water and extracted with 150 mL CHCl3 (3×50 mL). The CHCl3 extract was dried (MgSO4), and evaporated. The residue was recrystallized from THF-petroleum ether yielding 600 mg (47.4%), mp 270°-71° C. IR: (KBr): No C=O absorption at 1720 cm-1. H NMR (d6DMSO) δ 4.83 (s, C5H), Rf: silica gel EtOAc-EtOH-NH4OH (100:1:1) 0.18. Anal. Calcd for C17H20N2O4C, 64.54; H, 6.37; N, 8.86. Found C, 64.76; H, 6.5; N, 8.58.

Provenance & Evidence