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

HRID 1790440노트

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HRID 1790440 반응식
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

참가 물질

4

반응물 2

HCID 962WaterHCID 22037966HCID 22037966, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a3024f37927f46e597f945009b3e32ef
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071201B2

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