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Short Paper | Special issue | Vol 93, No. 2, 2016, pp.824-832
Published online, 17th November, 2015
DOI: 10.3987/COM-15-S(T)63
Synthesis of Noroxymorphone by N-Demethylation/ Intramolecular Acylation of Oxymorphone Catalyzed by Iron(II) Chloride

Mary Ann A. Endoma-Arias, Ales Machara, D. Phillip Cox, and Tomas Hudlicky*

*Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way St. Catharines, Ontario, L2R 3K4, Canada

Abstract

Oxymorphone was converted to its 3,14-diacetate and subjected to Fe(II)/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.