One-Pot Synthesis of Amino Alcohols from Styrenes

doi:10.6023/cjoc202002028

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2094-2098.DOI: 10.6023/cjoc202002028 Previous Articles Next Articles

苯乙烯一锅法合成氨基醇

何淑旺^a, 颜世强^b,c, 郭伟^c, 翟光喜^a, 张伟^b

a 山东大学药学院济南 250012;
b 复旦大学药学院上海 201203;
c 山东达因海洋生物制药股份有限公司山东威海 264300

收稿日期:2020-02-22 修回日期:2020-05-06 发布日期:2020-05-29
通讯作者: 翟光喜, 张伟 E-mail:professorgxzhai@126.com;zhangw416@fudan.edu.cn
基金资助:
国家重点研究与发展计划（No.2018YFC0310900）及国家科技重大专项“重大新药创制”（No.2018ZX09721003-008-026）资助项目.

One-Pot Synthesis of Amino Alcohols from Styrenes

He Shuwang^a, Yan Shiqiang^b,c, Guo Wei^c, Zhai Guangxi^a, Zhang Wei^b

a College of Pharmacy, Shandong University, Jinan 250012;
b School of Pharmacy, Fudan University, Shanghai 201203;
c Shandong Dyne Marine Biopharmaceutical Co., Ltd., Weihai, Shandong 264300

Received:2020-02-22 Revised:2020-05-06 Published:2020-05-29
Supported by:
Project supported by the National Key Research and Development Program of China (No. 2018YFC0310900) and the National Major Scientific and Technological Special Project for "Significant New Drugs Development" (No. 2018ZX09721003-008-026).

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Abstract

A two-step one-pot procedure for the synthesis of amino alcohols mediated by 1,3-dibromo-5,5-dimethylhydantoin (DBH) in aqueous acetone solution was developed. Styrene derivatives were treated with DBH at room temperature for 0.5~2.0 h followed by the addition of amine, affording the corresponding amino alcohols in 64%~88% yields. Tulobuterol, a widely used β2-adrenergic agonist, was prepared by this protocol in gram scale with the yield of 77%.

Key words: amino alcohol, one-pot synthesis, 1,3-dibromo-5,5-dimethylhydantoin, styrene

Cite this article

He Shuwang, Yan Shiqiang, Guo Wei, Zhai Guangxi, Zhang Wei. One-Pot Synthesis of Amino Alcohols from Styrenes[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2094-2098.

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苯乙烯一锅法合成氨基醇

One-Pot Synthesis of Amino Alcohols from Styrenes

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