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
收藏
页码：2676 / 2682
页数：7
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