methyl (1R,4S,6R)-2-oxo-3-azabicyclo[4.1.0]heptane-4-carboxylate | 1228431-62-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1R,4S,6R)-2-oxo-3-azabicyclo[4.1.0]heptane-4-carboxylate
• CAS: 1228431-62-6
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: TWEDRHLMZYUQJN-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1R,4S,6R)-2-oxo-3-azabicyclo[4.1.0]heptane-4-carboxylate 在 锂硼氢 、 硼烷四氢呋喃络合物 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 生成 1,1-dimethylethyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
  参考文献：
  名称：

  An Efficient Scalable Route for the Synthesis of Enantiomerically Pure tert-Butyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

  摘要：

  An efficient scalable route to synthesize the enantiomerically pure tert-butyl-(1R,4S,6R)-4-(hydrox)methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate is described. Compared to the original routes, significant improvements were made by using an innovative approach starting from commercially available chiral lactone. In this approach, one of the key steps described is an elegant epimerization/hydrolysis of the undesired diastereoisomer avoiding tedious purification. The chemistry has been scaled up to produce kilogram amounts of tert-butyl-(1R,4S,6R)-4-(hydroxymethyl)-3azabicyclo[4.1.0]heptane-3-carboxylate in 43% yield over nine chemical transformations.

  DOI：

  10.1021/op100164v
• 作为产物：
  描述：

  甲醇 、 1,1-dimethylethyl (1R,6R)-2-oxo-3-azabicyclo[4.1.0]heptane-4-carboxylate 在 potassium hydroxide 、 三甲基氯硅烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 methyl (1R,4S,6R)-2-oxo-3-azabicyclo[4.1.0]heptane-4-carboxylate
  参考文献：
  名称：

  An Efficient Scalable Route for the Synthesis of Enantiomerically Pure tert-Butyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

  摘要：

  An efficient scalable route to synthesize the enantiomerically pure tert-butyl-(1R,4S,6R)-4-(hydrox)methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate is described. Compared to the original routes, significant improvements were made by using an innovative approach starting from commercially available chiral lactone. In this approach, one of the key steps described is an elegant epimerization/hydrolysis of the undesired diastereoisomer avoiding tedious purification. The chemistry has been scaled up to produce kilogram amounts of tert-butyl-(1R,4S,6R)-4-(hydroxymethyl)-3azabicyclo[4.1.0]heptane-3-carboxylate in 43% yield over nine chemical transformations.

  DOI：

  10.1021/op100164v

文献信息

• NOVEL COMPOUNDS
  申请人：ALVARO Giuseppe

  公开号：US20100144760A1

  公开（公告）日：2010-06-10

  Disclosed are N-[(1R,4S,6R)-3-(2-pyridinylcarbonyl)-3-azabicyclo[4.1.0]hept-4-yl]methyl}-2-heteroarylamine derivatives and their use as pharmaceuticals.

  揭示了N-[(1R,4S,6R)-3-(2-吡啶基甲酰基)-3-氮杂双环[4.1.0]庚-4-基]甲基}-2-杂环芳胺衍生物及其作为药物的用途。
• An Efficient Scalable Route for the Synthesis of Enantiomerically Pure <i>tert</i>-Butyl-(1<i>R</i>,4<i>S</i>,6<i>R</i>)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
  作者：William M. Maton、Federica Stazi、Angelo Maria Manzo、Roberta Pachera、Arianna Ribecai、Paolo Stabile、Alcide Perboni、Nicola Giubellina、Fernando Bravo、Damiano Castoldi、Stefano Provera、Lucilla Turco、Simon Bryant、Pieter Westerduin、Roberto Profeta、Arnaldo Nalin、Emanuele Miserazzi、Simone Spada、Anna Mingardi、Mario Mattioli、Daniele Andreotti

  DOI：10.1021/op100164v

  日期：2010.9.17

  An efficient scalable route to synthesize the enantiomerically pure tert-butyl-(1R,4S,6R)-4-(hydrox)methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate is described. Compared to the original routes, significant improvements were made by using an innovative approach starting from commercially available chiral lactone. In this approach, one of the key steps described is an elegant epimerization/hydrolysis of the undesired diastereoisomer avoiding tedious purification. The chemistry has been scaled up to produce kilogram amounts of tert-butyl-(1R,4S,6R)-4-(hydroxymethyl)-3azabicyclo[4.1.0]heptane-3-carboxylate in 43% yield over nine chemical transformations.