Enantioselective Synthesis of ((1R,2R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate

被引：5

作者：

Ganesh, K. Ravi ^{[1
,2
]}

Pachore, Sharad S. ^{[1
]}

Pratap, T. V. ^{[1
]}

Umesh, K. ^{[1
]}

Rao, M. V. Basaveswara ^{[3
]}

Murthy, C. ^{[2
]}

Babu, M. Suresh ^{[1
]}

机构：

[1] Dr Reddys Labs Ltd, Custom Pharmaceut Serv, Technol Dev Ctr, Hyderabad 500049, Andhra Pradesh, India

[2] Vignans Fdn Sci Technol & Res Univ, Dept Sci & Humanities, Div Chem, Guntur, Andhra Pradesh, India

[3] Krishna Univ, Dept Chem, Machilipatnam, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2015年 / 45卷 / 23期

关键词：

Bis-mesylation; epimerization; esterification; hydrolysis; reduction; resolution;

D O I：

10.1080/00397911.2015.1074695

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 ((1R,2R)-cyclohexane-1,2-diyl)bis(methylene) dimethanesulfonate in overall good yield.

引用

页码：2676 / 2682

页数：7

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