Reacción #1269845

Ecuación de reacción

(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

Rendimiento 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

Rendimiento 94.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added dropwise
2. 2
   Otroquenched with water
3. 3
   ExtracciónThe mixture is extracted with CH2Cl2 (5×10 mL)
4. 4
   LavadoThe combined organic phase is washed with brine
5. 5
   Secadodried with anhydrous Na2SO4
6. 6
   FiltraciónAfter filtration
7. 7
   Otrothe filtrate is evaporated to dryness under reduced pressure

Procedimiento

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]+.

Fuente