2-[(4R,5R)-1-benzyl-5-methyl-2-oxoimidazolidin-4-yl]acetic acid | 1007218-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-[(4R,5R)-1-benzyl-5-methyl-2-oxoimidazolidin-4-yl]acetic acid
• CAS: 1007218-96-3
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: YPDLCMYUDJCLIG-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4R,5R)-1-benzyl-5-methyl-2-oxoimidazolidin-4-yl]acetic acid 在 盐酸 作用下， 反应 120.0h， 以99%的产率得到(4R,5R)-4-amino-1-benzyl-5-methyl-2-pyrrolidinone hydrochloride
  参考文献：
  名称：

  3-Aminopyrrolidines from α-Aminoacids:  Total Synthesis of (+)-Nemonapride from d-Alanine

  摘要：

  [GRAPHICS]The antipsychotic compound nemonapride 1 was synthesized in nine steps from D-alanine 2. The key steps for the synthesis of the 3-aminopyrrolidine moiety include a Birch reduction of a cyclic enaminoester and the reduction of a pyrrolidinone to the pyrrolidine 7. Final coupling with the benzoic acid derivative 9 gave 1 as a single enantio- and diastereomer.

  DOI：

  10.1021/jo702278k
• 作为产物：
  描述：

  (4R,5R)-4-amino-1-benzyl-5-methyl-2-pyrrolidinone hydrochloride 在 重铬酸吡啶 、 N,N-二甲基甲酰胺 作用下， 以100%的产率得到2-[(4R,5R)-1-benzyl-5-methyl-2-oxoimidazolidin-4-yl]acetic acid
  参考文献：
  名称：

  3-Aminopyrrolidines from α-Aminoacids:  Total Synthesis of (+)-Nemonapride from d-Alanine

  摘要：

  [GRAPHICS]The antipsychotic compound nemonapride 1 was synthesized in nine steps from D-alanine 2. The key steps for the synthesis of the 3-aminopyrrolidine moiety include a Birch reduction of a cyclic enaminoester and the reduction of a pyrrolidinone to the pyrrolidine 7. Final coupling with the benzoic acid derivative 9 gave 1 as a single enantio- and diastereomer.

  DOI：

  10.1021/jo702278k

文献信息

• 3-Aminopyrrolidines from α-Aminoacids:  Total Synthesis of (+)-Nemonapride from <scp>d</scp>-Alanine
  作者：Cam Thuy Hoang、Viet Hoang Nguyen、Valérie Alezra、Cyrille Kouklovsky

  DOI：10.1021/jo702278k

  日期：2008.2.1

  [GRAPHICS]The antipsychotic compound nemonapride 1 was synthesized in nine steps from D-alanine 2. The key steps for the synthesis of the 3-aminopyrrolidine moiety include a Birch reduction of a cyclic enaminoester and the reduction of a pyrrolidinone to the pyrrolidine 7. Final coupling with the benzoic acid derivative 9 gave 1 as a single enantio- and diastereomer.