978-76-7Relevant academic research and scientific papers
PROCESSES FOR PREPARING NOR-OPIOID COMPOUNDS AND OPIOID ANTAGONISTS BY ELECTROCHEMICAL N-DEMETHYLATION
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, (2021/12/31)
The present invention relates to a process for preparing a nor-opioid compound wherein an opioid precursor compound is electrochemically N-demethylated. The present invention further relates to a process for preparing an opioid antagonist compound, wherein an opioid precursor compound is electrochemically N-demethylated and the thus obtained nor-opioid compound is alkylated again at its secondary amine functional group.
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.
