Réaction #49303

Équation de réaction

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

hydrochloric acid

4-piperidineethanol

acetic acid

sodium triacetoxyborohydride

→

4-chloro-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperidinomethyl]indol-2-yl}isoindolinone

Rendement 110.3%

Solvants

acetonitrile

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Extractionby extracting with 1 mol/L hydrochloric acid
2. 2
   workup.ADDITIONThe aqueous layer was added with sodium carbonate
3. 3
   ExtractionThe mixture was extracted with ethyl acetate
4. 4
   LavageThe organic layer was washed with saturated brine
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   AutreThe solvent was evaporated under reduced pressure

Mode opératoire

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 4-piperidineethanol (94 mg, 0.73 mmol), acetic acid (0.168 mL, 2.93 mmol) and sodium triacetoxyborohydride (54 mg, 0.26 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. 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-(2-hydroxyethyl)piperidinomethyl]indol-2-yl}isoindolinone (42.2 mg).

Source