Direct Synthesis of Naltrexone by Palladium-Catalyzed N-Demethylation/Acylation of Oxymorphone: The Benefit of CH Activation and the Intramolecular Acyl Transfer from C-14 Hydroxy

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....

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Advanced synthesis & catalysis 2012-10, Vol.354 (14-15), p.2713-2718
Hauptverfasser:	Machara, Ales, Cox, D. Phillip, Hudlicky, Tomas
Format:	Artikel
Sprache:	eng
Schlagworte:	Activation Acylation Catalysis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms intramolecular acyl transfer Organic chemistry palladium-catalyzed N-demethylation Preparations and properties Reduction Synthesis synthesis of naltrexone Vitride™ reduction of amides
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	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.
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.201200677