(S)-3-benzoyloxy-N-benzylpyrrolidine hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-benzoyloxy-N-benzylpyrrolidine hydrochloride
• 英文别名: [(3S)-1-benzylpyrrolidin-3-yl] benzoate;hydrochloride
• 化学式: C₁₈H₁₉NO₂*ClH
• 分子量: 317.815
• InChiKey: WXGHRVWQXSNKQV-LMOVPXPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-benzoyloxy-N-benzylpyrrolidine hydrochloride 在 钯 异丙醇 、 异丙醚 作用下， 以 异丙醇 为溶剂， -10.0~55.0 ℃ 、59.47 MPa 条件下， 反应 14.5h， 以to provide the title pyrrolidine (7.3 Kg, 86.6%) as a colorless crystalline material的产率得到(S)-3-benzoyloxypyrrolidine hydrochloride
  参考文献：
  名称：

  Process for preparing hydroxypyrrolidinyl ethylamine compounds useful as kappa agonists

  摘要：

  一种制备化合物I:1或其光学异构体、外消旋或光学活性混合物的过程，该化合物可用作选择性kappa受体激动剂。

  公开号：

  US20020161241A1
• 作为产物：
  描述：

  苯甲酰氯 、 (S)-3-羟基-1-苄基吡咯烷 以 二氯甲烷 为溶剂， 反应 2.0h， 以96.6%的产率得到(S)-3-benzoyloxy-N-benzylpyrrolidine hydrochloride
  参考文献：
  名称：

  Efficient synthesis of the κ-opioid receptor agonist CJ-15,161: four stereospecific inversions at a single aziridinium stereogenic center

  摘要：

  An efficient four-step sequence has been developed for the synthesis of the kappa-opioid receptor agonist CJ-15,161. The process features four consecutive regioselective and stereospecific inversions at a single aziridinium stereogenic center, which leads to overall retention of stereochemistry, in a single operation. The chemistry is straightforward, practical and amenable to large-scale synthesis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00581-0

文献信息

• Process for preparing hydroxypyrrolidinyl ethylamine compounds useful as kappa agonists
  申请人：Pfizer Inc.

  公开号：US20020161241A1

  公开（公告）日：2002-10-31

  A process of preparing compounds having the formula I: 1 or an optical isomer or racemic or optically active mixture thereof, which are useful as selective kappa-receptor agonists.

  一种制备化合物I：1及其光学异构体或外消旋或光学活性混合物的过程，该化合物是作为选择性kappa-受体激动剂有用的。
• US6624313B2
  申请人：——

  公开号：US6624313B2

  公开（公告）日：2003-09-23
• Efficient synthesis of the κ-opioid receptor agonist CJ-15,161: four stereospecific inversions at a single aziridinium stereogenic center
  作者：Michel Couturier、John L. Tucker、Brian M. Andresen、Keith M. DeVries、Brian C. Vanderplas、Fumitaka Ito

  DOI：10.1016/s0957-4166(03)00581-0

  日期：2003.11

  An efficient four-step sequence has been developed for the synthesis of the kappa-opioid receptor agonist CJ-15,161. The process features four consecutive regioselective and stereospecific inversions at a single aziridinium stereogenic center, which leads to overall retention of stereochemistry, in a single operation. The chemistry is straightforward, practical and amenable to large-scale synthesis. (C) 2003 Elsevier Ltd. All rights reserved.