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Direct Synthesis of Naltrexone by Palladium‐Catalyzed N ‐Demethylation/Acylation of Oxymorphone: The Benefit of CH Activation and the Intramolecular Acyl Transfer from C‐14 Hydroxy
Author(s) -
Machara Ales,
Cox D. Phillip,
Hudlicky Tomas
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200677
Subject(s) - chemistry , oxymorphone , intramolecular force , acylation , naltrexone , palladium , demethylation , stereochemistry , medicinal chemistry , catalysis , organic chemistry , opioid , biochemistry , oxycodone , receptor , gene expression , dna methylation , gene
Oxymorphone was converted to naltrexone in three steps by palladium‐catalyzed oxidative N ‐demethylation and intramolecular acyl transfer from C‐14 hydroxy to N‐17. Vitride™ reduction of N ‐acylamide to N ‐alkylamine proceeded with concomitant reductive deprotection of C‐6 and O‐3 functionalities.