1-(Carbobenzyloxy)-trans-4-(methylamino)-3-pyrrolidinylpiperidine | 133671-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(Carbobenzyloxy)-trans-4-(methylamino)-3-pyrrolidinylpiperidine
• CAS: 133671-15-5
• 化学式: C₁₈H₂₇N₃O₂
• 分子量: 317.431
• InChiKey: ZBTISURGGSUACQ-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  44.81
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(Carbobenzyloxy)-trans-4-(methylamino)-3-pyrrolidinylpiperidine 在 sodium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 1-Benzyl-trans-4-(N-methyl-3',4'-dichlorophenylacetamido)-3-pyrrolidinylpiperidine
  参考文献：
  名称：

  trans-3,4-Diaminopiperidines. Azacyclohexane congeners of .kappa. agonist U-50488

  摘要：

  A variety of trans-3,4-diaminopiperidines were synthesized regio- and stereoselectively from 1-(carbobenzyloxy)-1,2,3,6-tetrahydropyridine. These compounds are structurally related to the selective kappa agonist U-50488. The two key reactions which determine the stereo- and regiochemistry of the final products involve the S(N)2 ring opening of an epoxide and an aziridinium species. Reaction of secondary amines with epoxide 3 led to ca. 1.5:1 mixtures of amino alcohols 4 and 5, while S(N)2 attack by methylamine on aziridinium intermediate 6 occurs diastereoselectively at C-4 to give diamines 7. Depending upon the isolation procedure, trimethylsilyl iodide cleavage of the carbobenzyloxy group in compounds 8 and 9 provides either N-benzyl compounds 12 and 13 or the unsubstituted piperidines 10 and 11.

  DOI：

  10.1021/jo00009a038
• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-(Carbobenzyloxy)-trans-4-(methylamino)-3-pyrrolidinylpiperidine
  参考文献：
  名称：

  trans-3,4-Diaminopiperidines. Azacyclohexane congeners of .kappa. agonist U-50488

  摘要：

  A variety of trans-3,4-diaminopiperidines were synthesized regio- and stereoselectively from 1-(carbobenzyloxy)-1,2,3,6-tetrahydropyridine. These compounds are structurally related to the selective kappa agonist U-50488. The two key reactions which determine the stereo- and regiochemistry of the final products involve the S(N)2 ring opening of an epoxide and an aziridinium species. Reaction of secondary amines with epoxide 3 led to ca. 1.5:1 mixtures of amino alcohols 4 and 5, while S(N)2 attack by methylamine on aziridinium intermediate 6 occurs diastereoselectively at C-4 to give diamines 7. Depending upon the isolation procedure, trimethylsilyl iodide cleavage of the carbobenzyloxy group in compounds 8 and 9 provides either N-benzyl compounds 12 and 13 or the unsubstituted piperidines 10 and 11.

  DOI：

  10.1021/jo00009a038