Facile Synthesis of Enantiomerically Pure 1-（5-Bromo-2-chlorophenyl）-1-（4-ethoxyphenyl）ethane

作     者：ZHANG Shuo WANG Wenjin LI Chuan LIU Peng XU Weiren TANG Lida WANG Jianwu ZHAO Guilong 

作者机构：School of Chemistry and Chemical Engineering Shandong University Jinan 250100 P.R.China Tianjin Key Laboratory of Molecular Design and Drug Discovery Tianjin Institute of Pharmaceutical ResearchTianjin 300193 P.R.China 

出 版 物：《Chemical Research in Chinese Universities》 (高等学校化学研究（英文版）)

年 卷 期：2014年第30卷第2期

页      面：250-256页

核心收录：

学科分类：081702[工学-化学工艺] 081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 0703[理学-化学] 070301[理学-无机化学] 

基　　金：Supported by the National Natural Science Foundation of China(No.21302141) and the Key Projects of Tianjin Science and Technology Support Plan China(No.10ZCKFSH01300) 

主　　题：Diarylethane Diastereomer Enantiomer Resolution SGLT2 inhibitor 

摘      要：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 *** 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,*** absolute configurations of the products were unambiguously determined by single-crystal X-ray diffractions of four key intermediates,9,10,13 and *** 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.