(S,R)-3a-methyl-hexahydro-pyrrolo[3,4-c]piperidine-2,5-dicarboxylic acid di-tert-butyl ester | 946828-12-2

• 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: (S,R)-3a-methyl-hexahydro-pyrrolo[3,4-c]piperidine-2,5-dicarboxylic acid di-tert-butyl ester
• 英文别名: ditert-butyl (3aS,7aR)-3a-methyl-1,3,4,6,7,7a-hexahydropyrrolo[3,4-c]pyridine-2,5-dicarboxylate
• CAS: 946828-12-2
• 化学式: C₁₈H₃₂N₂O₄
• 分子量: 340.463
• InChiKey: GCLXGJOFNOWOSB-UGSOOPFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,R)-3a-methyl-hexahydro-pyrrolo[3,4-c]piperidine-2,5-dicarboxylic acid di-tert-butyl ester 在 盐酸 、 甲醇 作用下， 反应 5.0h， 以92%的产率得到(S,R)-3a-methyl-pyrrolo[3,4-c]piperidine dihydrochloride
  参考文献：
  名称：

  Novel stereoselective synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine from glycine ethyl ester

  摘要：

  Asymmetric synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine is described herein. The key steps in this synthesis are the highly diastereo selective hydrogenation of an alkenyl nitrile through a hydroxyl-directed or sterically controlled hydrogenation, and the resolution of enantiomers using a chiral auxiliary. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.100
• 作为产物：
  描述：

  (3S)-4-cyanomethylene-3-hydroxymethyl-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 14.5h， 生成 (S,R)-3a-methyl-hexahydro-pyrrolo[3,4-c]piperidine-2,5-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Novel stereoselective synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine from glycine ethyl ester

  摘要：

  Asymmetric synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine is described herein. The key steps in this synthesis are the highly diastereo selective hydrogenation of an alkenyl nitrile through a hydroxyl-directed or sterically controlled hydrogenation, and the resolution of enantiomers using a chiral auxiliary. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.100