(S)-tert-Butyl 4-formyl-2-oxopyrrolidine-1-carboxylate | 1021167-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-tert-Butyl 4-formyl-2-oxopyrrolidine-1-carboxylate
• 英文别名: tert-butyl (4S)-4-formyl-2-oxopyrrolidine-1-carboxylate
• CAS: 1021167-89-4
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: VEHDZPGWAJTPNV-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-Butyl 4-formyl-2-oxopyrrolidine-1-carboxylate 、 triphenylphosphonio-1-methylethanide 以 四氢呋喃 为溶剂， 以60%的产率得到(R)-tert-butyl 4-(2-methylprop-1-en-1-yl)-2-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Stereoselective and efficient synthesis of (S)-pregabalin from d-mannitol

  摘要：

  A straightforward synthesis of (S)-pregabalin in 28% overall yield starting from D-mannitol acetonide, as a primary source of chirality, is presented. The process is suitable for large-scale synthesis and involves simple and high-yielding chemical transformations as well as low-cost commercially available reagents. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.005
• 作为产物：
  描述：

  (S)-tert-Butyl 4-((S)-1,2-dihydroxyethyl)-2-oxopyrrolidine-1-carboxylate 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到(S)-tert-Butyl 4-formyl-2-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Stereoselective and efficient synthesis of (S)-pregabalin from d-mannitol

  摘要：

  A straightforward synthesis of (S)-pregabalin in 28% overall yield starting from D-mannitol acetonide, as a primary source of chirality, is presented. The process is suitable for large-scale synthesis and involves simple and high-yielding chemical transformations as well as low-cost commercially available reagents. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.005

文献信息

• PROCESS FOR THE ENANTIOSELECTIVE PREPARATION OF PREGABALIN
  申请人：Ortuno Rosa M.

  公开号：US20100197939A1

  公开（公告）日：2010-08-05

  The invention provides a new enantioselective process for the preparation of (S)-pregabalin, or a pharmaceutical acceptable addition acid salt comprising: acid hydrolysis of the dioxolan ring of a chiral compound of general formula (I) to obtain compound of general formula (II); oxidation of compound (II) to obtain a compound of general formula (III) and transforming compound (III) into compound of general formula (IV); subjecting compound (IV) to basic hydrolysis to obtain a compound of general formula (V) which is reduced to obtain enantiomerically pure S-pregabalin. The invention also provides new chiral intermediates involved in the process.

  本发明提供了一种新的对映选择性工艺，用于制备（S）-普瑞巴林，或其药物可接受的酸盐，包括：对手性化合物（I）的二氧六环环的酸水解，以获得通式（II）的化合物；将化合物（II）氧化，以获得通式（III）的化合物，并将化合物（III）转化为通式（IV）的化合物；将化合物（IV）进行碱性水解，以获得通式（V）的化合物，然后还原化合物（V）以获得对映纯的S-普瑞巴林。本发明还提供了涉及该过程的新手性中间体。
• [EN] PROCESS FOR THE ENANTIOSELECTIVE PREPARATION OF PREGABALIN<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION ÉNANTIOSÉLECTIVE DE LA PRÉGABALINE
  申请人：ESTEVE LABOR DR

  公开号：WO2009010554A1

  公开（公告）日：2009-01-22

  The invention provides a new enantioselective process for the preparation of (S) -pregabalin, or a pharmaceutical acceptable addition acid salt comprising: acid hydrolysis of the dioxolan ring of a chiral compound of general formula (I) to obtain compound of general formula (II); oxidation of compound (II) to obtain a compound of general formula (III) and transforming compound (III) into compound of general formula (IV); subjecting compound (IV) to basic hydrolysis to obtain a compound of general formula (V) which is reduced to obtain enantiomerically pure S-pregabalin. The invention also provides new chiral intermediates involved in the process.
• Stereoselective and efficient synthesis of (S)-pregabalin from d-mannitol
  作者：Sandra Izquierdo、Jordi Aguilera、Helmut H. Buschmann、Mónica García、Antoni Torrens、Rosa M. Ortuño

  DOI：10.1016/j.tetasy.2008.03.005

  日期：2008.4

  A straightforward synthesis of (S)-pregabalin in 28% overall yield starting from D-mannitol acetonide, as a primary source of chirality, is presented. The process is suitable for large-scale synthesis and involves simple and high-yielding chemical transformations as well as low-cost commercially available reagents. (c) 2008 Elsevier Ltd. All rights reserved.