반응 #49256

반응 방정식

sodium carbonate

di-tert-butyldicarbonate

N-(2-hydroxyethyl)piperazine

acetic acid

sodium triacetoxyborohydride

5-Formylindole

→

5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indole

수율 132.2%

용매

water

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGby stirring at room temperature for 2.5 hours
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The organic layer was washed with saturated brine
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   기타The solvent was evaporated under reduced pressure
6. 6
   기타The residue was purified by flash column chromatography (chloroform/methanol=9/1, 4/1)

실험 절차

5-Formylindole (2.00 g, 13.8 mmol) was dissolved in acetonitrile (40 mL), and the solution was added with di-tert-butyldicarbonate (3.31 g, 15.2 mmol) and DMAP (16.8 mg, 0.138 mmol), followed by stirring at room temperature for 2.7 hours. The solution was added with a solution of N-(2-hydroxyethyl)piperazine (6.46 g, 49.6 mmol) in acetonitrile (15 mL), and acetic acid (14.2 mL, 248 mmol), then sodium triacetoxyborohydride (13.1 g, 62.0 mmol) was added thereto little by little, followed by stirring at room temperature for 2.5 hours. The reaction mixture was added with water and sodium carbonate to adjust the pH to 9, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (chloroform/methanol=9/1, 4/1) to obtain 5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indole (4.73 g, yield 95%).

출처