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

文献信息

• 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
  作者：Ariel L. L. Garcia、Marcos J. S. Carpes、Antonio C. B. M. de Oca、Marco A. G. dos Santos、César C. Santana、Carlos Roque D. Correia

  DOI：10.1021/jo0484880

  日期：2005.2.1

  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.