(1R,3aS,6aR)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid | 1393524-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3aS,6aR)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
• 英文别名: (3R,3aR,6aS)-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxylic acid
• CAS: 1393524-06-5
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: SFBZDQKMJLUZQF-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 在 仲丁基锂 、 potassium carbonate 、 鹰爪豆碱 作用下， 以 正己烷 、 甲基叔丁基醚 、 水 为溶剂， 反应 6.0h， 生成 (1S,3AR,6AS)-六氢环戊并[C]吡咯-1,2(1H)-二甲酸 2-叔丁酯 、 (1R,3aS,6aR)-2-(tert-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylic acid
  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

文献信息

• BIOCATALYTIC PROCESSES FOR THE PREPARATION OF SUBSTANTIALLY STEREOMERICALLY PURE FUSED BICYCLIC PROLINE COMPOUNDS
  申请人：Mijts Benjamin

  公开号：US20100063300A1

  公开（公告）日：2010-03-11

  The present disclosure provides substantially enantiomerically pure heterobicyclic compounds of the following structural formulas, wherein A, M, M′, and R 5 are as described herein, and to biocatalytic processes for their preparation, and to the enzymes used in those processes.

  本披露提供了下列结构式的基本对映纯的杂双环化合物，其中A、M、M'和R5如本文所述，并提供了用于它们制备的生物催化过程以及在这些过程中使用的酶。
• Substantially Stereomerically Pure Fused Bicyclic Proline Compounds and Processes for Preparing Boceprevir
  申请人：Lalonde James

  公开号：US20120289709A1

  公开（公告）日：2012-11-15

  The present disclosure provides substantially enantiomerically pure heterobicyclic compounds of the following structural formulas, wherein A, M, M′, and R 5 are as described herein, and to biocatalytic processes for their preparation, and to the enzymes used in those processes.

  本公开提供以下结构式的基本对映纯的杂双环化合物，其中A、M、M'和R5如本文所述，并提供其生物催化制备的过程，以及用于该过程的酶。
• US8178333B2
  申请人：——

  公开号：US8178333B2

  公开（公告）日：2012-05-15
• [EN] MULTICOMPONENT PROCESS FOR THE PREPARATION OF BICYCLIC COMPOUNDS<br/>[FR] PROCÉDÉ À MULTICOMPOSANTS POUR LA PRÉPARATION DE COMPOSÉS BICYCLIQUES
  申请人：CHEMO IBERICA SA

  公开号：WO2013178682A2

  公开（公告）日：2013-12-05

  It is described a general process, along with its possible variants, for the production of the compounds Telaprevir (I) and Boceprevir (II).
• 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.