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Premium Batch‐ and Continuous‐Flow Aerobic Oxidation of 14‐Hydroxy Opioids to 1,3‐Oxazolidines—A Concise Synthesis of Noroxymorphone
Author(s)
Gutmann Bernhard,
Weigl Ulrich,
Cox D. Phillip,
Kappe C. Oliver
Publication year2016
Publication title
chemistry – a european journal
Resource typeJournals
PublisherWiley
Abstract 14‐Hydroxymorphinone is converted to noroxymorphone, the immediate precursor of important opioid antagonists, such as naltrexone and naloxone, in a three‐step reaction sequence. The initial oxidation of the N ‐methyl group in 14‐hydroxymorphinone with in situ generated colloidal palladium(0) as the catalyst and molecular oxygen as the terminal oxidant constitutes the key transformation in this new route. This oxidation results in the formation of an unexpected oxazolidine ring structure. Subsequent hydrolysis of the oxazolidine under reduced pressure followed by hydrogenation in a packed‐bed flow reactor using palladium(0) as the catalyst provides noroxymorphone in high purity and good overall yield. To overcome challenges associated with gas–liquid reactions with molecular oxygen, the key oxidation reaction was translated to a continuous‐flow process.
Subject(s)catalysis , chemistry , hydrolysis , materials science , metallurgy , organic chemistry , oxazolidine , palladium , yield (engineering)
Language(s)English
SCImago Journal Rank1.687
H-Index242
eISSN1521-3765
pISSN0947-6539
DOI10.1002/chem.201601902

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