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52446-25-0Relevant articles and documents
Organophotocatalytic N-Demethylation of Oxycodone Using Molecular Oxygen
Cantillo, David,Chen, Yuesu,Glotz, Gabriel,Kappe, C. Oliver
, (2020)
N-Demethylation of oxycodone is one of the key steps in the synthesis of important opioid antagonists like naloxone or analgesics like nalbuphine. The reaction is typically carried out using stoichiometric amounts of toxic and corrosive reagents. Herein, we present a green and scalable organophotocatalytic procedure that accomplishes the N-demethylation step using molecular oxygen as the terminal oxidant and an organic dye (rose bengal) as an effective photocatalyst. Optimization of the reaction conditions under continuous flow conditions using visible-light irradiation led to an efficient, reliable, and scalable process, producing noroxycodone hydrochloride in high isolated yield and purity after a simple workup.
Electrochemical N-Demethylation of 14-Hydroxy Morphinans: Sustainable Access to Opioid Antagonists
Cantillo, David,Glotz, Gabriel,Kappe, C. Oliver
, p. 6891 - 6896 (2020/09/15)
The most challenging step in the preparation of many opioid antagonists is the selective N-demethylation of a 14-hydroxymorphinan precursor. This process is carried out on a large scale using stoichiometric amounts of hazardous chemicals like cyanogen bromide or chloroformates. We have developed a mild reagent- and catalyst-free procedure for the N-demethylation step based on the anodic oxidation of the tertiary amine. The ensuing intermediates can be readily hydrolyzed to the target nor-opioids in very good yields.
PROCESS FOR THE DEMETHYLAT I ON OF OXYCODONE AND RELATED COMPOUNDS
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Page/Page column 9-10, (2008/06/13)
A process is provided for the N-demethylation of certain morphinans by reaction with α-chloroethyl chloroformate followed by hydrolysis of the resulting intermediate.