高等学校化学学报

高等学校化学学报

• 研究快报 • 上一篇    下一篇

硅胶催化的选择性去除N-Boc保护基

张敏杰1,2, 袁修华1, 马丽1, 赵剑英1, 高连勋1   

  1. 1.中国科学院长春应用化学研究所, 高分子物理与化学国家重点实验室, 长春130022;2. 中国科学院研究生院, 北京 100049
  • 收稿日期:2007-06-12 修回日期:1900-01-01 出版日期:2007-12-10 发布日期:2007-12-10
  • 通讯作者: 高连勋

Selective Deprotection of N-Boc Catalyzed by Silica Gel

ZHANG Min-Jie1,2, YUAN Xiu-Hua1, MA Li1, ZHAO Jian-Ying1, GAO Lian-Xun1*   

  1. 1. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China; 2. Graduate School of Chinese Academy of Sciences, Beijing 100049, China
  • Received:2007-06-12 Revised:1900-01-01 Online:2007-12-10 Published:2007-12-10
  • Contact: GAO Lian-Xun

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被引次数

30

摘要： 发现了在回流的甲苯中, 以硅胶为催化剂, 多种N-Boc保护的伯胺、仲胺、氨基酸的氨基都可以迅速脱除Boc. 该方法具有条件温和、操作简便、反应时间短和产率高等优点. 同时, 其它常用的保护基Cbz和Fmoc等在同样的条件下不受影响.

关键词: N-Boc脱保护, 硅胶, 选择性脱保护

Abstract: As an important protective group of amines and amino acids, tert-butoxycarbonyl(Boc) group was extensively used in organic synthesis. Though many mild and selective reagents could be used, there is still a need for the development of a more simple and convenient method for deprotection. In this paper, a new method for the deprotection of N-Boc group with silica gel in refluxing toluene was reported. The reactions were mostly achieved in 5 h with high yields(75%—98%). N-Boc protected indoline and benzylamine, which are not deprotected with other mild method, could be deprotected with our method in good yields(89% and 95%, respectively). Additionally the deprotection of other carbamates such as Cbz, Fmoc and ethyl carbamate wasn’t observed under same conditions.

Key words: N-Boc deprotection, Silica gel, Selective deprotection

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