반응 #794454

반응 방정식

Diisopropyl azodicarboxylate

1-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

benzyl (trans-3-hydroxycyclobutyl)carbamate

triphenylphosphine

→

benzyl (trans-3-(1-cyclopropyl-2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)cyclobutyl)carbamate

수율 78.0%

용매

sodium bicarbonate

THF

반응 조건

후처리

1. 1
   온도the reaction mixture was warmed to room temperature
2. 2
   추출extracted with EtOAc
3. 3
   기타The organic layer was separated
4. 4
   세척washed with saturated aqueous sodium chloride
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The resulting crude product was purified by silica gel column chromatography
9. 9
   세척eluting with EtOAc in hexanes

실험 절차

1-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.740 g, 4.22 mmol), benzyl (trans-3-hydroxycyclobutyl)carbamate (0.934 g, 4.22 mmol), and triphenylphosphine (1.661 g, 6.33 mmol) were mixed in THF (15 mL) under an argon atmosphere and cooled to 0° C. Diisopropyl azodicarboxylate (1.244 mL, 6.33 mmol) was added dropwise via syringe, and the reaction mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield benzyl (trans-3-(1-cyclopropyl-2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)cyclobutyl)carbamate (1.244 g, 3.29 mmol, 78% yield) as an off-white solid. M+1: 379.2.

출처