7-fluoro-1-((1S,2R)-1-(3-fluorophenyl)-3-hydroxy-2-(methylamino)propyl)-3,3-dimethylindolin-2-one | 1186431-85-5

• 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: 7-fluoro-1-((1S,2R)-1-(3-fluorophenyl)-3-hydroxy-2-(methylamino)propyl)-3,3-dimethylindolin-2-one
• CAS: 1186431-85-5
• 化学式: C₂₀H₂₂F₂N₂O₂
• 分子量: 360.404
• InChiKey: GDCOKHLFGWMMNZ-IRXDYDNUSA-N

反应信息

• 作为产物：
  描述：

  (2S,3S)-3-((E)-7-fluoro-3,3-dimethyl-2-(methylimino)indolin-1-yl)-3-(3-fluorophenyl)propane-1,2-diol 在 氯化亚砜 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以70%的产率得到7-fluoro-1-((1S,2R)-1-(3-fluorophenyl)-3-hydroxy-2-(methylamino)propyl)-3,3-dimethylindolin-2-one
  参考文献：
  名称：

  Large-Scale Synthesis of a Selective Inhibitor of the Norepinephrine Transporter: Mechanistic Aspects of Conversion of Indolinone Diol to Indolinone Aminoalcohol and Process Implications

  摘要：

  Development of a scalable synthesis of WAY-315193 is described. Use of LiHMDS as a base and Ti(O-i-Pr)(4) as a Lewis acid was optimal for efficient and reproducible addition of indolinone anion to epoxyalcohol. Conversion of indolinone diol to indolinone aminoalcohol was achieved via monotosylation-methylamination. The possibility of selective formation of the amidine side product, as well as its utilization for alternative selective preparation of the target aminoalcohol, was demonstrated.

  DOI：

  10.1021/op900141r