(2R)-2-<(2S)-2-<(methylamino)methyl>piperidin-1-yl>-2-phenylethanol | 181872-12-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2-<(2S)-2-<(methylamino)methyl>piperidin-1-yl>-2-phenylethanol
• 英文别名: (2R)-2-[(2S)-2-(methylaminomethyl)piperidin-1-yl]-2-phenylethanol
• CAS: 181872-12-8
• 化学式: C₁₅H₂₄N₂O
• 分子量: 248.368
• InChiKey: OGLYHWNLQSDBKC-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-<(2S)-2-<(methylamino)methyl>piperidin-1-yl>-2-phenylethanol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到<(2S)-piperidin-2-yl>-N-methylmethanamine
  参考文献：
  名称：

  Asymmetric Synthesis. 39.¹ Synthesis of 2-(1-Aminoalkyl)piperidines via 2-Cyano-6-phenyl Oxazolopiperidine

  摘要：

  The asymmetric synthesis of a series of 2-(1-aminoalkyl) piperidines using (-)-2-cyano-6-phenyloxazolopiperidine 1 is described. LiAlH4 reduction of 1 followed by hydrogenolysis led to the diamine 3. The same strategy applied to C-2-methylated compound 7 afforded [(2S)-2-methylpiperidin-2-yl]methanamine (9). Addition of lithium derivatives to the cyano group of 1 resulted in the formation of an intermediate imino bicyclic system (11a-c) which could be diastereoselectively reduced to substituted diamino alcohols 13a-c. The addition of an excess of PhLi to 1 in the presence of LiBr furnished disubstituted amine 19, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine (22).

  DOI：

  10.1021/jo960910s
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 (2R)-2-<(2S)-2-<(methylamino)methyl>piperidin-1-yl>-2-phenylethanol
  参考文献：
  名称：

  Diazaborolidines, a new class of enantioselective organoboron catalytic agents.

  摘要：

  Diazaborolidines 6 and 9, derived from 2-aminomethyl-piperidine, have been prepared in an optically pure form from 2-cyano-6-phenyl oxazolopiperidine 3. The best results for the asymmetric reduction of acetophenone (yield>95%, 72% ee) have been obtained with BH3.Me2S in the presence of 9a as a chiral catalyst.

  DOI：

  10.1016/s0957-4166(00)80097-x

文献信息

• Diazaborolidines, a new class of enantioselective organoboron catalytic agents.
  作者：Olivier Froelich、Martine Bonin、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1016/s0957-4166(00)80097-x

  日期：1993.11

  Diazaborolidines 6 and 9, derived from 2-aminomethyl-piperidine, have been prepared in an optically pure form from 2-cyano-6-phenyl oxazolopiperidine 3. The best results for the asymmetric reduction of acetophenone (yield>95%, 72% ee) have been obtained with BH3.Me2S in the presence of 9a as a chiral catalyst.
• Asymmetric Synthesis. 39.¹ Synthesis of 2-(1-Aminoalkyl)piperidines <i>via</i> 2-Cyano-6-phenyl Oxazolopiperidine
  作者：Olivier Froelich、Patrice Desos、Martine Bonin、Jean-Charles Quirion、Henri-Philippe Husson、Jieping Zhu

  DOI：10.1021/jo960910s

  日期：1996.1.1

  The asymmetric synthesis of a series of 2-(1-aminoalkyl) piperidines using (-)-2-cyano-6-phenyloxazolopiperidine 1 is described. LiAlH4 reduction of 1 followed by hydrogenolysis led to the diamine 3. The same strategy applied to C-2-methylated compound 7 afforded [(2S)-2-methylpiperidin-2-yl]methanamine (9). Addition of lithium derivatives to the cyano group of 1 resulted in the formation of an intermediate imino bicyclic system (11a-c) which could be diastereoselectively reduced to substituted diamino alcohols 13a-c. The addition of an excess of PhLi to 1 in the presence of LiBr furnished disubstituted amine 19, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine (22).