3-(5-Bromopyridine-3-carbonyl)-1-ethenylpyrrolidin-2-one | 201292-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(5-Bromopyridine-3-carbonyl)-1-ethenylpyrrolidin-2-one
• CAS: 201292-62-8
• 化学式: C₁₂H₁₁BrN₂O₂
• 分子量: 295.136
• InChiKey: KWBCAENGKVAZHG-UHFFFAOYSA-N

物化性质

• 沸点：
  473.2±45.0 °C(Predicted)
• 密度：
  1.607±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-Bromopyridine-3-carbonyl)-1-ethenylpyrrolidin-2-one 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 copper(l) iodide 、 甲酸 、 sodium hydride 、 potassium carbonate 、 甲烷 、 三苯基膦 作用下， 以 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 60.5h， 生成 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine
  参考文献：
  名称：

  A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (S)-(−)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)

  摘要：

  An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis(trimethylsilyl)amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5-bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new heteroaryl-alkyne cross-coupling protocol for the introduction of the ethyne moiety in (S)-2. The preparation of enantiomerically pure (S)-2 was accomplished via a combination of enantioselective reduction of imine 5 and crystallization of enantiomerically enriched 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (7) as the dibenzoyl-L-tartaric acid salt.

  DOI：

  10.1021/jo971572d
• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 5-溴烟酸乙酯 在 lithium hexamethyldisilazane 作用下， 生成 3-(5-Bromopyridine-3-carbonyl)-1-ethenylpyrrolidin-2-one
  参考文献：
  名称：

  A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (S)-(−)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)

  摘要：

  An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis(trimethylsilyl)amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5-bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new heteroaryl-alkyne cross-coupling protocol for the introduction of the ethyne moiety in (S)-2. The preparation of enantiomerically pure (S)-2 was accomplished via a combination of enantioselective reduction of imine 5 and crystallization of enantiomerically enriched 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (7) as the dibenzoyl-L-tartaric acid salt.

  DOI：

  10.1021/jo971572d

文献信息

• J. Med. Chem. 1996, 39, 3235-3237
  作者：

  DOI：——

  日期：——
• A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (<i>S</i>)-(−)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)
  作者：Leo S. Bleicher、Nicholas D. P. Cosford、Audrey Herbaut、J. Stuart McCallum、Ian A. McDonald

  DOI：10.1021/jo971572d

  日期：1998.2.1

  An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis(trimethylsilyl)amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5-bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new heteroaryl-alkyne cross-coupling protocol for the introduction of the ethyne moiety in (S)-2. The preparation of enantiomerically pure (S)-2 was accomplished via a combination of enantioselective reduction of imine 5 and crystallization of enantiomerically enriched 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (7) as the dibenzoyl-L-tartaric acid salt.