Synthesis of RP 48497, an Impurity of Eszopiclone

Molecules

Yu Sha¹  Lei Zhang¹  Gui-Jie Du²  Jian Ren¹ 

[1] Key Lab of New Drug Design and Discovery of Liaoning Province, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China; E-mails:;Jinzhou Jiutai Pharmaceutical Co. Ltd, Jinzhou 121012, P.R. China; E-mail:

关键词: RP 48497;    eszopiclone;    quality control;   

DOI  :  10.3390/molecules13081817

来源: mdpi

【 摘 要 】

RP 48497 is a photodegradation product of eszopiclone, a non-benzodiazepine sedative-hypnotic used in the treatment of insomnia. We report herein the first synthesis of RP 48497 via reduction, chlorination, and recyclization of 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydropyrrolo[3,4-b]pyrazin-5-one (3), a key intermediate in the synthesis of eszopiclone. The structure of RP 48497 was confirmed by its ¹H-NMR and MS data. The mechanism of the reduction step in the synthesis of RP 48497 was also studied and the key parameters were determined. These findings should be important for quality control purposes in the manufacture of eszopiclone.

【 授权许可】

CC BY   
© 2008 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.