Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Patent metadata

Field	Value
Publication number	US-2019152893-A1
Application number	US-201916258802-A
Country	US
Kind code	A1
Filing date	Jan 28, 2019
Priority date	Jul 24, 2015
Publication date	May 23, 2019
Grant date	—

Abstract

Provided herein are methods and intermediates for making (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

First claim

What is claimed is:

1 . A method for preparing a compound of formula (3),

the method comprising contacting a compound of formula (1),

with a compound of formula (2),

in the presence of a Lewis acid in a solvent.

2 . The method of claim 1 , wherein the Lewis acid is AlCl 3 .

3 . The method of claim 1 , wherein the solvent is DCM.

4 . A method for preparing a compound of formula (7),

the method comprising contacting a compound of formula (6),

with (+)-dibenzoyl-D-tartaric acid monohydrate in a solvent.

5 . The method of claim 4 , wherein the solvent is MeOH.

6 . A compound of formula (7),

Assignees

• Celgene Corp

Inventors

• Connolly Terrence Joseph
• Man Hon-Wah
• Nagarajan Periyandi
• Rajendiran Chinnapillai
• Venkateswarlu Jasti

Classifications

• C07C269/04

  from amines with formation of carbamate groups · CPC title

• C07C51/09

  from carboxylic acid esters or lactones · CPC title

• C07C67/347

  by addition to unsaturated carbon-to-carbon bonds · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title

• C07C209/88

  Separation of optical isomers · CPC title