PROCESS FOR PRODUCTION OF DELTA-9-TETRAHYDROCANNABINOL

• US 20110263878A1
• Filed: 05/16/2011
• Published: 10/27/2011
• Est. Priority Date: 09/29/2005
• Status: Active Grant

• Current Assignee: Albany Molecular Research Incorporated
• Original Assignee: Albany Molecular Research Incorporated
• Inventors: BURDICK, David C., Biolatto, Betina, Collier, Steven J., Meckler, Harold
• Granted Patent: US 8,106,244 B2
• Time in Patent Office: Days
• US Class Current: 549/390
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 29/00 Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
• CPC Class Codes: C07C 35/16 Inositols
• CPC Class Codes: C07C 37/16 by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
• CPC Class Codes: C07C 39/23 polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
• CPC Class Codes: C07C 67/343 by increase in the number of carbon atoms
• CPC Class Codes: C07C 69/94 of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings

Abstract

The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula:

where R₈, R₉, and R₁₀ are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R₁, R₂, and R₃ defined herein.

Claims

1. A process for preparation of a product compound of the formula:

2. The process according to claim 1, wherein the carbonate base is K₂CO₃.

3. The process according to claim 1, wherein X is hydrogen.

4. The process according to claim 1 further comprising:

reacting a starting material compound of the formula;

5. The process according to claim 4, wherein the conditions effective to form the second intermediate compound include reacting the starting material compound with thiophenol.