Réaction #1269845

Équation de réaction

(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

Rendement 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

Rendement 94.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis added dropwise
2. 2
   Autrequenched with water
3. 3
   ExtractionThe mixture is extracted with CH2Cl2 (5×10 mL)
4. 4
   LavageThe combined organic phase is washed with brine
5. 5
   Séchagedried with anhydrous Na2SO4
6. 6
   FiltrationAfter filtration
7. 7
   Autrethe filtrate is evaporated to dryness under reduced pressure

Mode opératoire

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]+.

Source