반응 #49305

반응 방정식

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

sodium carbonate

isonipecotamide

acetic acid

sodium triacetoxyborohydride

→

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

수율 70.0%

용매

acetonitrile

water

반응 조건

후처리

1. 1
   추출The mixture was extracted with ethyl acetate
2. 2
   세척The organic layer was washed with saturated brine
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   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 (40.0 mg, 0.0974 mmol) was dissolved in acetonitrile (3 mL), and the solution was treated with isonipecotamide (154 mg, 1.20 mmol), acetic acid (0.896 mL, 15.7 mmol) and sodium triacetoxyborohydride (188 mg, 0.887 mmol). The reaction mixture was added with water and sodium 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-(4-methoxycarbonylpiperidinomethyl)indol-2-yl]isoindolinone (35.5 mg, yield 70%).

출처