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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Decoration of the aromatic ring of dihydrocodeinone (hydrocodone) and 14-hydroxydihydrocodeinone (oxycodone)
Michael L Wilson1, Patrick J Carroll, David R Dalton
1Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. michael.wilson@temple.edu
Abstract:
Improved protocols for the preparation of 1-bromodihydrocodeinone (1-bromohydrocodone) and 1-bromo-14-hydroxydihydrocodeinone (1-bromooxycodone) and synthesis of the corresponding 1-chloro and 1-iodo derivatives have been achieved using the corresponding N-halosuccinimides in acidic milieu. The corresponding 1-carboethoxy derivative of 14-hydroxydihydrocodeinone (1-carboethoxyoxycodone) has been prepared by Pd-catalyzed reaction with carbon monoxide in ethanol. The ester was hydrolyzed to the corresponding zwitterionic amino acid.
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