7-Aminotricyclo[3.3.1.03,7]nonan-3-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Aminotricyclo[3.3.1.03,7]nonan-3-ol
• 化学式: C₉H₁₅NO
• mdl: MFCD01940404
• 分子量: 153.22
• InChiKey: UJFVTUYVISKDKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-Aminotricyclo[3.3.1.03,7]nonan-3-ol 以94%的产率得到
  参考文献：
  名称：

  Camps Pelayo, Font-Bardia Merce, Munoz-Torrero Diego, Solans Xavier, Liebigs. Ann, (1995) N 3, S 523-535

  摘要：

  DOI：
• 作为产物：
  描述：

  Bicyclo[3.3.1]nonane-3,7-dione monooxime 生成 7-Aminotricyclo[3.3.1.03,7]nonan-3-ol
  参考文献：
  名称：

  Camps Pelayo, Munoz-Torrero Diego, Tetrahedron Lett, 35 (1994) N 19, S 3187-3190

  摘要：

  DOI：

文献信息

• [EN] ONE-POT PROCESS TO OBTAIN A PYRROLIDINE-2-CARBONITRILE INTERMEDIATE COMPOUND AND INDUSTRIAL SCALE TELESCOPIC PROCESS TO PREPARE (2S)-1-[N-(3-HYDROXYADAMANTAN-1-YL)GLYCYL]-2-PYRROLIDINECARBONITRILE (VILDAGLIPTIN) USING SAME<br/>[FR] PROCÉDÉ MONOTOPE PERMETTANT D'OBTENIR UN COMPOSÉ INTERMÉDIAIRE PYRROLIDINE-2-CARBONITRILE ET PROCÉDÉ TÉLESCOPIQUE À L'ÉCHELLE INDUSTRIELLE PERMETTANT DE PRÉPARER DU (2S)-1-[N-(3-HYDROXYADAMANTAN-1-YL)GLYCYL]-2-PYRROLIDINECARBONITRILE (VILDAGLIPTINE) L'UTILISANT
  申请人：SAVOI GUILHERME

  公开号：WO2022003405A1

  公开（公告）日：2022-01-06

  An industrial scale telescopic process for preparing (2S)-1-[N-(3-hydroxyadamantan-1-yl)glycyl]-2-pyrrolidinecarbonitrile (Vildagliptin) of formula:, comprising: (a) reacting the compound of formula: with an excess of a compound of formula:, wherein X and Y are, independently, a halogen selected from Cl, Br and I, preferably Cl, thereby the compound is chloroacetyl chloride, in a high-boiling polar solvent, such that the reaction product is intermediate compound: wherein X is as defined above, and is obtained in a single step; (b) quenching the reaction by the addition of water and a base; (c) extracting the reaction product in a polar organic solvent and evaporating the extraction solvent thus obtaining a product which mostly comprises the intermediate compound; (d) dissolving the product comprising the intermediate compound by the addition of an organic solvent; and (e) reacting the intermediate compound with 3-amino-1-adamantanol, in the presence of potassium carbonate and potassium iodide to obtain crude Vildagliptin from the reaction mixture. Also disclosed is a one-pot process to obtain the intermediate compound (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile.