(2R,3R)-tert-butyl 3-amino-2-phenylpiperidine-1-carboxylate

• 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: (2R,3R)-tert-butyl 3-amino-2-phenylpiperidine-1-carboxylate
• 英文别名: tert-Butyl cis-3-amino-2-phenylpiperidine-1-carboxylate；tert-butyl (2R,3R)-3-amino-2-phenylpiperidine-1-carboxylate
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: GQOAORJRRSLOQA-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-tert-butyl 3-amino-2-phenylpiperidine-1-carboxylate 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 (+)-(2S,3S)-3-(2-methoxybenzylamino)-2-phenylpiperidine dihydrochloride
  参考文献：
  名称：

  Diastereoconvergent Synthesis of trans-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process

  摘要：

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

  DOI：

  10.1021/ol5020812
• 作为产物：
  描述：

  methyl (4S)-4-(t-butyldimethylsilyloxy)-5-oxopentanoate 在 吡啶 、 lithium aluminium tetrahydride 、 硼烷 、 甲氧基胺盐酸盐 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 copper(II) sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 (2R,3R)-tert-butyl 3-amino-2-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  Diastereoconvergent Synthesis of trans-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process

  摘要：

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.

  DOI：

  10.1021/ol5020812

文献信息

• Diastereoconvergent Synthesis of <i>trans</i>-5-Hydroxy-6-Substituted-2-Piperidinones by Addition–Cyclization–Deprotection Process
  作者：Chang-Mei Si、Wei Huang、Zhen-Ting Du、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1021/ol5020812

  日期：2014.8.15

  A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by alpha-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.