(R)-2-[2-(tert-butyldimethylsilanyloxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester | 1150660-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-2-[2-(tert-butyldimethylsilanyloxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R)-2-[2-[tert-butyl(dimethyl)silyl]oxyethyl]piperidine-1-carboxylate
• CAS: 1150660-09-5
• 化学式: C₁₈H₃₇NO₃Si
• 分子量: 343.582
• InChiKey: LJGIFRMRGBPLCG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-[2-(tert-butyldimethylsilanyloxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester 、 硫酸二甲酯 在 四甲基乙二胺 、 (2-methylpropyl)lithium 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以39%的产率得到(2R,6S)-2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-6-methylpiperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (−)-dumetorine, and (+)- and (−)-epidihydropinidine

  摘要：

  The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2008.12.008
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (R)-1-N-BOC-哌啶-2-乙醇 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(R)-2-[2-(tert-butyldimethylsilanyloxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (−)-dumetorine, and (+)- and (−)-epidihydropinidine

  摘要：

  The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2008.12.008

文献信息

• Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (−)-dumetorine, and (+)- and (−)-epidihydropinidine
  作者：Daniele Passarella、Sergio Riva、Gabriele Grieco、Francesco Cavallo、Begoña Checa、Federica Arioli、Elena Riva、Daniela Comi、Bruno Danieli

  DOI：10.1016/j.tetasy.2008.12.008

  日期：2009.2

  The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively. (C) 2008 Elsevier Ltd. All rights reserved