(1R,6S)-methyl 2-oxo-3-azabicyclo[4.1.0]heptane-1-carboxylate | 1820752-43-9

• 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: (1R,6S)-methyl 2-oxo-3-azabicyclo[4.1.0]heptane-1-carboxylate
• 英文别名: Methyl (1R,6S)-2-oxo-3-azabicyclo[4.1.0]heptane-1-carboxylate
• CAS: 1820752-43-9
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: RZENDDBGQVPZKU-SVGQVSJJSA-N

反应信息

• 作为反应物：
  描述：

  (1R,6S)-methyl 2-oxo-3-azabicyclo[4.1.0]heptane-1-carboxylate 在 4-二甲氨基吡啶 、 锂硼氢 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 23.0h， 生成 (1R,6S)-tert-butyl 1-(hydroxymethyl) 3-azabicyclo[4.1.0]heptane-3-carboxylate
  参考文献：
  名称：

  Synthesis of racemic and enantiopure 3,4-methanonipecotic acid

  摘要：

  The synthesis of both racemic and enantiomerically pure (1R,6S)-3,4-methanonipecotic acid, a cyclopropane-containing 8-amino acid, which is a valuable building block for drug discovery, is described. The synthetic scheme commences from natural (S)-malic acid and allows for the preparation of the title compound in 12 steps in 28% overall yield. A novel approach to the racemic 3,4-methanonipecotic acid, which relies on a Simmons-Smith cyclopropanation as the key step, was also developed. In this case, the product was obtained in 8 steps and 38% total yield. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2015.09.015
• 作为产物：
  描述：

  (S)-dimethyl 2-(2-azidoethyl)cyclopropane-1,1-dicarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 19.0h， 以76%的产率得到(1R,6S)-methyl 2-oxo-3-azabicyclo[4.1.0]heptane-1-carboxylate
  参考文献：
  名称：

  Synthesis of racemic and enantiopure 3,4-methanonipecotic acid

  摘要：

  The synthesis of both racemic and enantiomerically pure (1R,6S)-3,4-methanonipecotic acid, a cyclopropane-containing 8-amino acid, which is a valuable building block for drug discovery, is described. The synthetic scheme commences from natural (S)-malic acid and allows for the preparation of the title compound in 12 steps in 28% overall yield. A novel approach to the racemic 3,4-methanonipecotic acid, which relies on a Simmons-Smith cyclopropanation as the key step, was also developed. In this case, the product was obtained in 8 steps and 38% total yield. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2015.09.015