반응 #49306

반응 방정식

4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

hydrochloric acid

ethylamine

acetic acid

sodium triacetoxyborohydride

→

4-chloro-7-[1-(tert-butoxycarbonyl)-5-(ethylaminomethyl)indol-2-yl]isoindolinone

수율 83.0%

용매

acetonitrile

ethyl acetate

반응 조건

후처리

1. 1
   추출by extracting with 1 mol/L hydrochloric acid
2. 2
   workup.ADDITIONThe aqueous layer was added with sodium hydrogen carbonate
3. 3
   추출The mixture was extracted with ethyl acetate
4. 4
   세척The organic layer was washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The solvent was evaporated under reduced pressure

실험 절차

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (41.2 mg, 0.100 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 70% aqueous ethylamine-solution (0.192 mL, 2.42 mmol), acetic acid (0.345 mL, 6.03 mmol) and sodium triacetoxyborohydride (170 mg, 0.802 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and ethyl acetate, followed by extracting with 1 mol/L hydrochloric acid. The aqueous layer was added with sodium hydrogen carbonate to adjust the pH to 9. The mixture was 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 to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(ethylaminomethyl)indol-2-yl]isoindolinone (36.4 mg, yield 83%).

출처