N-demethylation of morphinan alkaloids

US10626120B2 · kind B2 · utility

Assignee

• NORAMCO, LLC · US

Inventors

• Dominique Roberge · Sierre, CH
• Petteri Elsner · Brig, CH
• Christian Oliver KAPPE · Graz, AT
• Bernhard Gutmann · Graz, AT
• Ulrich Weigl · Hilzingen, DE
• Douglas Phillip Cox · Eagleville, US

Key dates

• Filing date: Apr 21, 2017
• Grant date: Apr 21, 2020
• Expiry date: Apr 21, 2037

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D489/08
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present disclosure relates to N-demethylation of a compound containing a tertiary N-methylamine, including for example a morphinan alkaloid, in a continuous flow system. In particular, the present disclosure relates to N-demethylation of oxymorphone-3,14-diacetate or 14-hydroxymorphinone-3,14-diacetate using highly active catalytic palladium (0) in a continuous flow system under elevated temperature and pressure condition. The methodology can be utilized towards the synthesis of noroxymorphone via aerobic palladium-catalyzed continuous flow N-demethylation.