meso-3,4-isopropylidenedioxypyrrolidine hydrotosylate | 383417-91-2

• 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: meso-3,4-isopropylidenedioxypyrrolidine hydrotosylate
• 英文别名: (3aR,6aS)-tetrahydro-2,2-dimethyl-4H-1,3-dioxolo-[4,5-c]pyrrole, p-toluenesulfonate；Cis-(3,4-Diolacetonide)-pyrrolidine p-methylbenzosulphonic acid salt；(3aS,6aR)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole;4-methylbenzenesulfonic acid
• CAS: 383417-91-2
• 化学式: C₇H₈O₃S*C₇H₁₃NO₂
• 分子量: 315.39
• InChiKey: MWVRHAJNTQBCPJ-KNCHESJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3aR,6aS)-5-benzyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyrrole 在 10% palladium hydroxide on charcoal 、 氢气 作用下， 以 甲醇 、 丁酮 为溶剂， 15.0~30.0 ℃ 、515.03 kPa 条件下， 反应 7.0h， 生成 meso-3,4-isopropylidenedioxypyrrolidine hydrotosylate
  参考文献：
  名称：

  Use of DOE for Rapid Development of a Red-Al Reduction Process for the Synthesis of 3,4-Isopropylidenedioxypyrrolidine Hydrotosylate

  摘要：

  Statistical design of experiments (DOE) was used to rapidly optimize Red-Al reduction of an imide to produce, after deprotection and salt formation, 3,4-isopropylidenedioxypyrrolidine hydrotosylate (1), an intermediate in the synthesis of Ingliforib. A Red-Al reduction process was successfully scaled to produce multikilogram quantities of 1, thus demonstrating a safer and more economical process. Further development resulted in an optimized procedure, which not only avoided borane reduction but also allowed the three-step procedure to be performed without isolation of the intermediates, solvent exchange, or distillation.

  DOI：

  10.1021/op040204q

文献信息

• Use of DOE for Rapid Development of a Red-Al Reduction Process for the Synthesis of 3,4-Isopropylidenedioxypyrrolidine Hydrotosylate
  作者：Asaf R. Alimardanov、Mark T. Barrila、Frank R. Busch、James J. Carey、Michel A. Couturier、Curtis Cui

  DOI：10.1021/op040204q

  日期：2004.11.1

  Statistical design of experiments (DOE) was used to rapidly optimize Red-Al reduction of an imide to produce, after deprotection and salt formation, 3,4-isopropylidenedioxypyrrolidine hydrotosylate (1), an intermediate in the synthesis of Ingliforib. A Red-Al reduction process was successfully scaled to produce multikilogram quantities of 1, thus demonstrating a safer and more economical process. Further development resulted in an optimized procedure, which not only avoided borane reduction but also allowed the three-step procedure to be performed without isolation of the intermediates, solvent exchange, or distillation.