Synthesis of Noroxymorphone by N-demethylation/ Intramolecular Acylation of Oxymorphone Catalyzed by Iron(II) Chloride

Abstract

Oxymorphone was converted to its 3,14-diacetate and subjected to Fe(11)/t-BuOOH-catalyzed N-demethylation that occurred with concomitant acyl migration from the C-14 hydroxyl to the N-17 nitrogen. The resulting diacetyl compound was hydrolyzed in dilute sulfuric acid to noroxymorphone in good yield.

Keywords

• oxymorphone
• noroxymorphone
• N-demethylation
• acyl migration