3-(4-methoxy-phenyl)-4-(methoxy-phenyl-acetoxy)-pyrrolidine-1-carboxylic acid benzyl ester | 936229-95-7

• 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: 3-(4-methoxy-phenyl)-4-(methoxy-phenyl-acetoxy)-pyrrolidine-1-carboxylic acid benzyl ester
• CAS: 936229-95-7
• 化学式: C₂₈H₂₉NO₆
• 分子量: 475.541
• InChiKey: WFKIODTYAABKCQ-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxy-phenyl)-4-(methoxy-phenyl-acetoxy)-pyrrolidine-1-carboxylic acid benzyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以40%的产率得到
  参考文献：
  名称：

  Synthesis of conformationally restricted acetylcholine analogues. Comparing lipase-mediated resolution with simulated moving bed chromatography of arylated β-hydroxy-pyrrolidines

  摘要：

  The enantiodivergent synthesis of new, conformationally restricted acetylcholine analogues was accomplished using arylated endocyclic enecarbamates as key intermediates. Stereoselective hydroboration of the aryl enecarbamates provided the corresponding aryl-ss-hydroxy-pyrrolidines. Acetylation, deprotection, followed by N-bismethylation, led to the desired betaine products. The kinetic resolution of the intermediate alcohols was performed by lipase-mediated hydrolysis of its acetate derivatives, resulting in excellent enantioselectivities (E > 100). An enzymatic enantiopreference predicted by the Kazlauskas's model was confirmed following Riguera's protocol. Finally, chromatographic resolution of racemic alcohol 5a was evaluated by semi-preparative scale chiral simulated moving bed chromatography and its performance compared with biocatalysis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.030
• 作为产物：
  描述：

  3-吡咯烷-1-甲酸苄酯 在 palladium diacetate 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 Pseudomonas cepacia AK lipase 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 phosphate buffer 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 731.0h， 生成 3-(4-methoxy-phenyl)-4-(methoxy-phenyl-acetoxy)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of conformationally restricted acetylcholine analogues. Comparing lipase-mediated resolution with simulated moving bed chromatography of arylated β-hydroxy-pyrrolidines

  摘要：

  The enantiodivergent synthesis of new, conformationally restricted acetylcholine analogues was accomplished using arylated endocyclic enecarbamates as key intermediates. Stereoselective hydroboration of the aryl enecarbamates provided the corresponding aryl-ss-hydroxy-pyrrolidines. Acetylation, deprotection, followed by N-bismethylation, led to the desired betaine products. The kinetic resolution of the intermediate alcohols was performed by lipase-mediated hydrolysis of its acetate derivatives, resulting in excellent enantioselectivities (E > 100). An enzymatic enantiopreference predicted by the Kazlauskas's model was confirmed following Riguera's protocol. Finally, chromatographic resolution of racemic alcohol 5a was evaluated by semi-preparative scale chiral simulated moving bed chromatography and its performance compared with biocatalysis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.030