Synthetic Communications p. 2676 - 2682 (2015)
Update date:2022-08-17
Topics:
Ravi Ganesh
Pachore, Sharad S.
Pratap
Umesh
Basaveswara Rao
Murthy
Suresh Babu
A concise, economical, and highly enantioselective synthesis of bismesylate intermediate of lurasidone HCl, an antipsychotic, has been developed. The key steps involved in the synthesis are thionyl chloride-catalyzed esterification of tetrahydrophthalic anhydride in MeOH, epimerization of cis to trans isomer, hydrolysis of the diester, resolution of the diacid, reduction with Red-Al, and finally bismesylation of the corresponding diol, which provided the desired intermediate ((1 R,2 R)-cyclohexane-1,2-diyl)bis(methylene) dimethanesulfonate in overall good yield.
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