반응 #49401

반응 방정식

4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

hydrochloric acid

3-hydroxypiperidine

acetic acid

sodium triacetoxyborohydride

→

4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(3-hydroxypiperidinomethyl)indol-2-yl]isoindolinone

수율 34.3%

용매

acetonitrile

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   세척The organic layer was washed with saturated aqueous sodium carbonate solution and 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 147, 4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (104 mg, 0.188 mmol) was dissolved in acetonitrile (5.2 mL), and the solution was treated with 3-hydroxypiperidine (76.0 mg, 0.752 mmol), acetic acid (0.215 mL, 3.76 mmol) and sodium triacetoxyborohydride (160 mg, 0.752 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-[3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(3-hydroxypiperidinomethyl)indol-2-yl]isoindolinone (40.9 mg, yield 34%).

출처