Facile synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethane

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• 作者：Shuo Zhang (1) (2)
  Wenjin Wang (2)
  Chuan Li (2)
  Peng Liu (2)
  Weiren Xu (2)
  Lida Tang (2)
  Jianwu Wang (1)
  Guilong Zhao (2)
  
• 关键词：Diarylethane ; Diastereomer ; Enantiomer ; Resolution ; SGLT2 inhibitor
• 刊名：Chemical Research in Chinese Universities
• 出版年：2014
• 出版时间：April 2014
• 年：2014
• 卷：30
• 期：2
• 页码：250-256
• 全文大小：603 KB
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• 作者单位：Shuo Zhang (1) (2)
  Wenjin Wang (2)
  Chuan Li (2)
  Peng Liu (2)
  Weiren Xu (2)
  Lida Tang (2)
  Jianwu Wang (1)
  Guilong Zhao (2)
  
  1. School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China
  2. Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin, 300193, P. R. China
  
• ISSN：2210-3171

文摘

A facile 7-step procedure for the synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethanes[(R)-2 and(S)-2] that started from (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone 3 was developed. The key step was the resolution of 2-(5-bromo-2-chlorophenyl)-2-(4-ethoxyphenyl)acetic acid 6 by crystallizations of its L- and D-menthyl esters 7 and 8 from petroleum ether to give optically pure enantiomers 9 and 10, respectively. The absolute configurations of the products were unambiguously determined by single-crystal X-ray diffractions of four key intermediates, 9, 10, 13 and 14. This procedure is characterized by inexpensiveness, scalability and ability to produce two individual enantiomers of a diarylethane with unambiguously determined absolute configurations and high enantiomeric purities.