反応 #1269845

反応方程式

(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

収率 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

収率 94.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONis added dropwise
2. 2
   その他quenched with water
3. 3
   抽出The mixture is extracted with CH2Cl2 (5×10 mL)
4. 4
   洗浄The combined organic phase is washed with brine
5. 5
   乾燥dried with anhydrous Na2SO4
6. 6
   ろ過After filtration
7. 7
   その他the filtrate is evaporated to dryness under reduced pressure

実験手順

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]+.

出典