Реакция #1269845

Уравнение реакции

(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

Выход 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

Выход 94.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONis added dropwise
2. 2
   Другоеquenched with water
3. 3
   ЭкстракцияThe mixture is extracted with CH2Cl2 (5×10 mL)
4. 4
   ПромывкаThe combined organic phase is washed with brine
5. 5
   Сушкаdried with anhydrous Na2SO4
6. 6
   ФильтрацияAfter filtration
7. 7
   Другоеthe filtrate is evaporated to dryness under reduced pressure

Методика

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]+.

Источник