Reaktion #49307

Reaktionsgleichung

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

hydrochloric acid

2-piperidine methanol

acetic acid

sodium triacetoxyborohydride

→

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

Ausbeute 57.2%

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 hydrogen carbonate
3. 3
   ExtraktionThe mixture was extracted 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 (50.9 mg, 0.124 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with 2-piperidine methanol (63.8 mg, 0.554 mmol), acetic acid (0.284 mL, 4.96 mmol) and sodium triacetoxyborohydride (158 mg, 0.745 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 hydrogen 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-[2-(hydroxymethyl)piperidinomethyl]indol-2-yl}isoindolinone (36.2 mg, yield 57%).

Quelle