(1R,5S,11aS)-3-isobutyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine | 1351992-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (1R,5S,11aS)-3-isobutyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine
• 英文别名: (1R,2S,9S)-11-(2-methylpropyl)-7,11-diazatricyclo[7.3.1.02,7]tridecane
• CAS: 1351992-73-8
• 化学式: C₁₅H₂₈N₂
• 分子量: 236.401
• InChiKey: XFSDSMMLVQTMRF-ZNMIVQPWSA-N

物化性质

• 沸点：
  307.4±10.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cytisine 在 platinum(IV) oxide 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 22.0 ℃ 、446.08 kPa 条件下， 反应 50.0h， 生成 (1R,5S,11aS)-3-isobutyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine
  参考文献：
  名称：

  Stereoselective Lithiation and Carboxylation of Boc-Protected Bicyclopyrrolidine: Synthesis of a Key Building Block for HCV Protease Inhibitor Telaprevir

  摘要：

  A stereoselective process for the manufacture of bicyclopyrrolidine 7 to 2 has been developed. The process utilizes a stereoselective lithiation/carboxylation sequence. The achiral diamine ligand DPBP induces excellent diastereocontrol, and resolution with (S)-THNA provides the corresponding salt of 8 in high er and dr. Subsequent processing of 8 gives 2 as the oxalate salt in an overall yield of 27% from 7 (based on total molar charge of 7). Compound 2 was obtained with high chemical, and chiral purities. The process was successfully demonstrated on >100 kg scale.

  DOI：

  10.1021/op500040j
• 作为试剂：
  描述：

  二氧化碳 、 在 甲基叔丁基醚 、 (1R,5S,11aS)-3-isobutyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine 、 仲丁基锂 作用下， 以 正庚烷 为溶剂， 反应 8.5h， 以25%的产率得到(S)-1,2,3,4-tetrahydronaphthalen-1-aminium (1S,3aR,6aS)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
  参考文献：
  名称：

  [EN] PROCESSES AND INTERMEDIATES
  [FR] PROCÉDÉS ET PRODUITS INTERMÉDIAIRES

  摘要：

  公开号：

  WO2011153423A3

文献信息

• PROCESSES AND INTERMEDIATES
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20130096277A1

  公开（公告）日：2013-04-18

  A process for preparing enantioselectively a compound of formula I-1a or I-1b: over a compound of formulas I-2-I-7:
• [EN] PROCESSES AND INTERMEDIATES<br/>[FR] PROCÉDÉS ET PRODUITS INTERMÉDIAIRES
  申请人：VERTEX PHARMA

  公开号：WO2011153423A3

  公开（公告）日：2013-03-07
• Stereoselective Lithiation and Carboxylation of Boc-Protected Bicyclopyrrolidine: Synthesis of a Key Building Block for HCV Protease Inhibitor Telaprevir
  作者：Gerald J. Tanoury、Minzhang Chen、Yong Dong、Raymond Forslund、Valdas Jurkauskas、Andrew D. Jones、Daniel Belmont

  DOI：10.1021/op500040j

  日期：2014.10.17

  A stereoselective process for the manufacture of bicyclopyrrolidine 7 to 2 has been developed. The process utilizes a stereoselective lithiation/carboxylation sequence. The achiral diamine ligand DPBP induces excellent diastereocontrol, and resolution with (S)-THNA provides the corresponding salt of 8 in high er and dr. Subsequent processing of 8 gives 2 as the oxalate salt in an overall yield of 27% from 7 (based on total molar charge of 7). Compound 2 was obtained with high chemical, and chiral purities. The process was successfully demonstrated on >100 kg scale.