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US 11,192,847 B2Granted
Methods of synthesis of (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
AssigneeCelgene Corporation
InventorsTerrence Joseph Connolly, Hon-Wah Man
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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.
Claims3
A method for preparing a compound of formula (7),
- the method comprising (a) contacting a compound of formula (1),
- with a compound of formula (2),
- in the presence of a Lewis acid in a solvent, to provide a compound of formula (3),
- (b) contacting the compound of formula (3) of step (a) with an aqueous base to provide a compound of formula (4),
- (c) contacting the compound of formula (4) of step (b) with DMF and a chlorinating agent in an organic solvent, followed by treatment of the resulting acid chloride derivative with aqueous ammonia to provide a compound of formula (5),
- (d) contacting the compound of formula (5) of step (c) with an aqueous solution of NaOH and NaOCl to provide a compound of formula (6),
- (e) contacting the compound of formula (6) of step (d) with (+)-dibenzoyl-D-tartaric acid monohydrate in a solvent to provide a compound of formula (7).
4 more elements
Dependencies are inferred from the claim text.