Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (04): 486-489. Previous Articles     Next Articles

Full Papers

含氨基的金刚烷桥头二取代化合物合成研究

谢炳玉1,郭建维*,1,刘卅2,彭进平1   

  1. (1广东工业大学轻工化工学院 广州 510006)
    (2华南理工大学材料科学与工程学院 广州 510640)
  • 收稿日期:2010-08-29 修回日期:2010-10-06 发布日期:2010-11-23
  • 通讯作者: 谢炳玉 E-mail:xiebingyu.515@163.com
  • 基金资助:

    金刚烷及其应用技术研究开发

Synthesis of Briddgehead Bis-substituted Amino-adamantane Compounds

Xie Bingyu1 Guo Jianwei*,1 Liu Sa2 Peng Jinping1   

  1. (1 Faculty of Chemical Engineering & Light Industry, Guangdong University of Technology, Guangzhou 510006)
    (2 College of Material Science & Engineering, Southchina University of Technology, Guangzhou 510640)
  • Received:2010-08-29 Revised:2010-10-06 Published:2010-11-23

3-Amino-1-adamantanol, a key intermediate of anti-diabetic drug, was successfully synthesized via bromization, azido, Curtius rearrangement and hydrolysis processes by using adamantane carboxylic acid as the starting raw material. The overall yield of 3-amino-1-adamantanol was 34%. 3-Amino- 1-adamantane carboxylic acid hydrochloride, an anti-neoplastic agent,was synthesized from adamantane carboxylic acid by Ritter, hydrolysis reaction in total yield of 73%. The structures of products were identified by elemental analysis, IR, MS, 1H NMR, etc. In addition, the possible reaction mechanisms were respectively proposed.

Key words: 3-amino-1-adamantanol, 3-amino-1-adamantane carboxylic acid hydrochloride, synthesis

CLC Number: