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Synthesis of RP 48497, an Impurity of Eszopiclone
Key Lab of New Drug Design and Discovery of Liaoning Province, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China
Jinzhou Jiutai Pharmaceutical Co. Ltd, Jinzhou 121012, P.R. China
* Author to whom correspondence should be addressed.
Received: 5 June 2008; in revised form: 8 August 2008 / Accepted: 12 August 2008 / Published: 22 August 2008
Abstract: 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.
Keywords: RP 48497; eszopiclone; quality control
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MDPI and ACS Style
Sharov, Y.; Zhang, L.; Du, G.-J.; Ren, J.; Cheng, M.-S. Synthesis of RP 48497, an Impurity of Eszopiclone. Molecules 2008, 13, 1817-1821.
Sharov Y, Zhang L, Du G-J, Ren J, Cheng M-S. Synthesis of RP 48497, an Impurity of Eszopiclone. Molecules. 2008; 13(8):1817-1821.
Sharov, Yu; Zhang, Lei; Du, Gui-Jie; Ren, Jian; Cheng, Mao-Sheng. 2008. "Synthesis of RP 48497, an Impurity of Eszopiclone." Molecules 13, no. 8: 1817-1821.