Reaktion #49299

Reaktionsgleichung

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

Ausbeute 103.7%

Lösungsmittel

acetonitrile

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionby extracting with 1 mol/L hydrochloric acid
2. 2
   workup.ADDITIONThe aqueous layer was added with sodium carbonate
3. 3
   Extraktionby extracting with ethyl acetate
4. 4
   WaschenThe organic layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure

Vorschrift

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).

Quelle