Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 14-15, Pages 2706-2712Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200676
Keywords
Burgess reagent; N-demethylation of oxycodone and oxymorphone; N-oxides of oxycodone and oxymorphone; synthesis of naltrexone; naloxone; and nalbuphone
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Funding
- Noramco, Inc.
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Research Chair Program
- Canada Foundation for Innovation (CFI)
- TDC Research, Inc.
- TDC Research Foundation
- Brock University
- Ontario Partnership for Innovation and Commercialization (OPIC)
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N-Oxides derived from oxycodone and O-acyloxymorphone were treated with the Burgess reagent to provide the corresponding oxazolidines in excellent yields. Oxazolidines derived from O-acyloxymorphone were further hydrolyzed to noroxymorphone, whose alkylation furnished naltrexone, naloxone, and nalbuphone, which can be converted to nalbuphine, the mixed agonist-antagonist analgesic. The entire sequence from oxymorphone to the various antagonists was reduced to three one-pot operations, proceeding in excellent overall yields. In addition, quaternary salts of the oxazolidines with allyl or cyclopropylmethyl groups in fixed equatorial configurations were synthesized. Complete spectral and experimental data are provided for all compounds.
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