Reaktion #816422

Reaktionsgleichung

ethyl chlorocarbonate

tert-butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

diisopropylethylamine

→

title compound

Ausbeute 72.0%

5-tert-butyl 1-ethyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Ausbeute 72.0%

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto reach room temperature
2. 2
   SonstigeThe obtained mixture was evaporated to dryness under vacuum
3. 3
   Extraktionthe resulting residue extracted with ethyl acetate (AcOEt) and water
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried over sodium sulfate
6. 6
   Sonstigeevaporated to dryness
7. 7
   SonstigeThe mixture was purified by flash-chromatography (eluent: ethyl acetate/cyclohexane 4/6 to 7/3)

Vorschrift

A solution of ethyl chlorocarbonate (8.9 ml, 93 mmol) in tetrahydrofuran (THF, 250 ml) was slowly added to a mixture of tert-butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (20 g, 89 mmol) and diisopropylethylamine (DIEA, 92 ml, 528 mmol) in THF (500 ml) at 0-5° C. The reaction was kept at the same temperature for two hours then allowed to reach room temperature and stirred overnight. The obtained mixture was evaporated to dryness under vacuum, and the resulting residue extracted with ethyl acetate (AcOEt) and water. The organic layer was separated, dried over sodium sulfate and evaporated to dryness. The mixture was purified by flash-chromatography (eluent: ethyl acetate/cyclohexane 4/6 to 7/3) to give 19 g of the title compound as a white solid. [M+H]+ 297

Quelle