41135-98-2Relevant articles and documents
Direct and simple O-demethylation of thebaine to oripavine
Coop, Andrew,Lewis, John W.,Rice, Kenner C.
, p. 6774 - 6774 (1996)
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Design and Development of Pd-Catalyzed Aerobic N-Demethylation Strategies for the Synthesis of Noroxymorphone in Continuous Flow Mode
Gutmann, Bernhard,Cantillo, David,Weigl, Ulrich,Cox, D. Phillip,Kappe, C. Oliver
supporting information, p. 914 - 927 (2017/02/15)
Strategies for the generation of noroxymorphone from 14-hydroxymorphinone are presented. Noroxymorphone is the key intermediate in the synthesis of various opioid antagonists, including naloxone, naltrexone, and nalmefene, as well as mixed agonists-antagonists such as nalbuphine. The transformation requires removal of the N-methyl group from the naturally occurring opiates and double-bond hydrogenation. The pivotal reaction step thereby is an N-methyl oxidation with colloidal palladium(0) as catalyst and pure oxygen as terminal oxidant. The reaction produces a 1,3-oxazolidine intermediate, which can be readily hydrolyzed to the corresponding secondary amine. Different reaction sequences and the use of various phenol protecting groups were explored. The most direct route consumes only H2, O2, and H2O as stoichiometric reagents and produces only H2O as a byproduct. Challenges inherent to gas/liquid reactions with oxygen as oxidant have been addressed by developing a continuous flow process.
PROCESS FOR OBTAINING 3,14-DIACETYLOXYMORPHONE FROM ORIPAVINE
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Page/Page column 20; 21, (2018/01/17)
The present invention relates to a new process for obtaining 3,14-diacetyloxymorphone from oripavine, a process to transform the obtained 3,14-diacetyloxymorphone into a noroxymorphone and a process to transform said noroxymorphone into naloxone, naltrexone, nalbuphine, nalfurafine or nalmefene.