Water → 6-methoxy-2,3-dihydro-1H-indole

HRID 1790440ノート

反応式

HRID 1790440 の反応式
FC1C=CC(CCN2CCC([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[CH:16]=[CH:15]3)CC2)=CC=1.O>FC(F)(F)C(O)=O>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17]([CH2:16][CH2:15][NH:14]2)=[CH:18][CH:19]=1

参加物

4

反応物 2

HCID 962WaterHCID 22037966HCID 22037966、化合物

生成物 1

HCID 64275496-methoxy-2,3-dihydro-1H-indole収率 98.4%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
0 °C

実験手順

A 1 M solution (0.18 ml) of a borane/tetrahydrofuran complex was added dropwise at 0° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methoxyindole (24 mg) in trifluoroacetic acid (1 ml) over 2 min followed by stirring at 0° C. for 30 min. Af ter the completion of the reaction, water (0.1 ml) was added thereto and the resulting reaction solution was concentrated under reduced pressure. The resulting residue was dissolved in a 2 N aqueous solution of sodium hydroxide and stirred at room temperature for 10 min. The mixture was extracted with methylene chloride. The organic layer was separated and dried over magnesium sulfate. After concentrating the solvent under reduced pressure, the resulting residue was purified by preparative TLC to give 1-[1-(4-fluorophenethyl)piperidin-4-yl)]-6-methoxyindoline (10 mg) (yield: 35%).

後処理

  1. additionwas added
  2. customthe resulting reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in a 2 N aqueous solution of sodium hydroxide
  5. stirringstirred at room temperature for 10 min
  6. extractionThe mixture was extracted with methylene chloride
  7. customThe organic layer was separated
  8. dry with materialdried over magnesium sulfate
  9. concentrationAfter concentrating the solvent under reduced pressure
  10. customthe resulting residue was purified by preparative TLC

出典と根拠

ORDレコード
ord-a3024f37927f46e597f945009b3e32ef
出典データセット
uspto-grants-2006_07
特許番号
US07071201B2

反応ノート

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