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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 7: 2094 - 2098

DOI: https://doi.org/10.6023/cjoc202002028

One-Pot Synthesis of Amino Alcohols from Styrenes

  • He Shuwang ,
  • Yan Shiqiang ,
  • Guo Wei ,
  • Zhai Guangxi ,
  • Zhang Wei
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  • 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 date: 2020-02-22

  Revised date: 2020-05-06

  Online 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 . DOI: 10.6023/cjoc202002028

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