Sequential Benzylic Oxidation of Naloxone 3-Methyl Ether |
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| Authors: | Gary A Cain Spencer Drummond Jr |
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| Institution: | 1. Chemical &2. Physical Sciences, The DuPont Pharmaceuticals Company , P.O. Box 80336, Wilmington, Delaware, 19880--0336 |
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| Abstract: | Naloxone 3-methyl ether was selectively oxidized by treatment with cerium ammonium nitrate in aqueous acetonitrile at ambient temperature to provide the 10-(S)-hydroxy adduct. The stereochemistry of the oxidation product was proven by single crystal X-ray structure determination. The Dess-Martin periodinane further oxidized the 10-hydroxy to the 10-keto analog. Deprotection formed 10-ketonaloxone as an analytical reference standard. |
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