Reaktion #49301

Reaktionsgleichung

glycineamide hydrochloride

triethylamine

acetic acid

sodium triacetoxyborohydride

hydrochloric acid

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

→

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

Ausbeute 120.6%

Lösungsmittel

ethyl acetate

acetonitrile

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
   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 (30.0 mg, 0.0730 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with glycineamide hydrochloride (96 mg, 0.87 mmol), triethylamine (0.243 mL, 1.74 mmol), acetic acid (0.252 mL, 4.40 mmol) and sodium triacetoxyborohydride (231 mg, 1.09 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-[(aminocarbonylmethyl)aminomethyl]indol-2-yl}isoindolinone (41.3 mg).

Quelle