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

A method for preparing a compound of formula (A),

• the method comprising the steps of:
• (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),
• (f) contacting the compound of formula (7) of step (e) with an aqueous base, followed by treatment of the resulting free base with Boc2O in an organic solvent to provide a compound of formula (8),
• (g) contacting the compound of formula (8) of step (f) with a mixture of a reducing agent, a chiral auxiliary and a Lewis acid in a solvent, followed by treatment with an oxidant in the presence of a base to provide a compound of formula (9),
• and
• (h) contacting the compound of formula (9) of step (g) with a solution of hydrochloric acid in a solvent to provide the compound of formula (A).