1-(tert-butoxycarbonyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-ol | 844873-53-6

• 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: 1-(tert-butoxycarbonyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-ol
• 英文别名: Tert-butyl 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-hydroxypyrrolidine-1-carboxylate
• CAS: 844873-53-6
• 化学式: C₂₁H₃₁NO₅
• 分子量: 377.481
• InChiKey: DEJQMPWGRNTTMU-UHFFFAOYSA-N

物化性质

• 沸点：
  502.4±50.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-ol 在 盐酸 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 咯利普兰
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880
• 作为产物：
  描述：

  2-cyclopentyloxy-4-methoxyaniline hydrochloride 在 盐酸 、 palladium diacetate 、 水 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 1.25h， 生成 1-(tert-butoxycarbonyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-ol
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880