반응 #1269845

반응 방정식

(3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one

p-toluenesulfonylmethyl isocyanide

Sodium hydride

→

crude product

수율 94.0%

(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one

수율 94.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONis added dropwise
2. 2
   기타quenched with water
3. 3
   추출The mixture is extracted with CH2Cl2 (5×10 mL)
4. 4
   세척The combined organic phase is washed with brine
5. 5
   건조dried with anhydrous Na2SO4
6. 6
   여과After filtration
7. 7
   기타the filtrate is evaporated to dryness under reduced pressure

실험 절차

Sodium hydride (95%, 112 mg, 4.44 mmol) is suspended in 3 mL of anhydrous THF, and then a mixture of (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one (283 mg, 1.48 mmol) and p-toluenesulfonylmethyl isocyanide (97%, 347 mg, 1.77 mmol) in 5 mL of anhydrous THF is added dropwise. The mixture is stirred at room temperature for an hour, and then quenched with water. The mixture is extracted with CH2Cl2 (5×10 mL). The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration, the filtrate is evaporated to dryness under reduced pressure to give crude product (320 mg, yield 94%) as brown solids, which is used for the next reaction without further purification. MS (ESI) m/z 231.1 [M+H]+.

출처