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A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics
Synthetic Communications ( IF 2.1 ) Pub Date : 2021-08-06 , DOI: 10.1080/00397911.2021.1961155
Yuyan Yang 1 , Hua Li 1 , Zhonglin You 1 , Xingxian Zhang 1
Affiliation  

Abstract

A novel and enantioselective synthesis of (S)-2-pipecolic acid (5) has been achieved from Oppolzer’s sultam (1) and ethyl N-(diphenylmethylene)glycinate (2) as readily available starting materials. The highly stereoselective alkylation of chiral glycine intermediate (3) with 1,4-dibromobutane afforded the key backbone of (S)-2-pipecolic acid (5) in one-step that was utilized into the preparation of the local anesthetics mepivacaine, ropivacaine and bupivacaine.



中文翻译:

(S)-2-哌可酸的便捷且高度对映选择性合成:有效获取卡因麻醉剂

摘要

已经从 Oppolzer 的 sultam ( 1 ) 和N- (二苯基亚甲基) 甘氨酸乙酯 ( 2 ) 作为容易获得的起始材料实现了 ( S )-2-哌啶酸 ( 5 )的新型和对映选择性合成。手性甘氨酸中间体 ( 3 ) 与 1,4-二溴丁烷高度立体选择性烷基化,一步得到 (S)-2-哌啶酸 ( 5 )的关键骨架,用于制备局部麻醉剂甲哌卡因、罗哌卡因和布比卡因。

更新日期:2021-08-06
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