IP Library Granted Patent US 11,040,932
Granted Patent B2
US 11,040,932 · App. 16/599,026 · Granted Jun 22, 2021

Synthesis of cannabigerol

Inventors: Thomas Smeltzer (Longmont, CO); Robert Davis (Boulder, CO); Sean Colvin (Gunbarrel, CO); Jacob Black (New Haven, CT)
Assignee: Treehouse Biotech, Inc.
C07C39/19B01J27/08B01J27/128B01J27/138B01J27/232B01J31/0225C07C37/11C07C37/685C07C43/285C07F7/081
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Quick Facts
Patent No.
US 11,040,932
App. No.
16/599,026
Granted
Jun 22, 2021
Kind
B2
Abstract

Multiple methods of synthesizing cannabigerol are presented. Combining olivetol with geraniol derivatives are provided. Cross-coupling methods of combing functionalized resorcinols are provided. Useful intermediates are formed during such cross-coupling steps.

Claims (12)

1. A method comprising:

providing a first compound having the structure

combining the first compound with a second compound having the structure:

in a solvent to form a solution;

adding a suitable cross coupling metal catalyst to the solution to form an active mixture; and

reacting the active mixture to form a reacting mixture, wherein the reacting mixture contains a detectable amount of a third compound having the structure:

wherein R 1 and R 3 each are selected from the group consisting of: SEM, MOM, Me, Bn, TBS, and hydrogen;

wherein Z is selected from the group consisting of: boronate group, boronic acid, iodide, and bromide; and

wherein Y is selected from the group consisting of: iodide, bromide, a boronate group, and boronic acid group.

2. The method of claim 1 , wherein the solvent is selected from the group consisting of: N,N-dimethylacetamide, toluene, 1-butanol, tetrahydrofuran, and mixtures thereof.

3. The method of claim 1 , wherein the catalyst is selected from the group consisting of: XPhos-Pd-G3 ((2-Dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate); SPhos-Pd-G2 (Chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); cataCXium-A-Pd-G3 (Mesylate[(di(1-adamantyl)-n-butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II)); APhos-Pd-G3 ([4-(Di-tert-butylphosphino)-N,N-dimethylaniline-2-(2′-aminobiphenyl)]palladium(II) methanesulfonate); P(Cy)3-Pd-G3 ([(Tricyclohexylphosphine)-2-(2′-aminobiphenyl)]palladium(II) methanesulfonate); PEPPSI-IPent (Dichloro[1,3-bis(2,6-Di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II)); and Pd(PPh3)4 (Palladium-tetrakis(triphenylphosphine)).

4. The method of claim 1 , wherein Y is pinacol boronate.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 12, 2021
From: CANOPY HOLDINGS, LLC
To: TREEHOUSE BIOTECH, INC.
Reel/Frame 056221/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 27, 2019
From: SMELTZER, THOMAS; DAVIS, ROBERT; COLVIN, SEAN; BLACK, JACOB
To: CANOPY HOLDINGS, LLC
Reel/Frame 051378/0589 →
Continuity (2)
Provisional Application 62743982 · Oct 10, 2018
Related Publication 20200115306A1 · Apr 16, 2020
Cited By (1)
US 12,433,903