(S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropan-1-amine | 1103518-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropan-1-amine
• 英文别名: (S)-3-(5-Fluoro-1H-indol-3-yl)-2-methylpropan-1-amine；(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropan-1-amine
• CAS: 1103518-35-9
• 化学式: C₁₂H₁₅FN₂
• 分子量: 206.263
• InChiKey: NLRRJAHVVQTEBE-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-quinaldine dioxine brosylate 、 (S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropan-1-amine 在 4-二甲氨基吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以28%的产率得到WAY-262398
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085
• 作为产物：
  描述：

  (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropan-1-amine
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085

文献信息

• First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist
  作者：Antonia Nikitenko、Asaf Alimardanov、Jay Afragola、Jean Schmid、Livia Kristofova、Deborah Evrard、Nicole T. Hatzenbuhler、Vasilios Marathias、Gary Stack、Steve Lenicek、John Potoski

  DOI：10.1021/op8002085

  日期：2009.1.16

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.