반응 #49299

반응 방정식

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

hydrochloric acid

morpholine

acetic acid

sodium triacetoxyborohydride

→

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

수율 103.7%

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 carbonate
3. 3
   추출by extracting 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 (30.0 mg, 0.0730 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with morpholine (0.100 mL, 1.15 mmol), acetic acid (0.084 mL, 1.5 mmol) and sodium triacetoxyborohydride (154 mg, 0.727 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 carbonate to adjust the pH to 9, followed by extracting 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-(morpholinomethyl)indol-2-yl]isoindolinone (36.5 mg).

출처