Reaktion #1269845

Reaktionsgleichung

(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

Ausbeute 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

Ausbeute 94.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added dropwise
2. 2
   Sonstigequenched with water
3. 3
   ExtraktionThe mixture is extracted with CH2Cl2 (5×10 mL)
4. 4
   WaschenThe combined organic phase is washed with brine
5. 5
   Trocknendried with anhydrous Na2SO4
6. 6
   FiltrationAfter filtration
7. 7
   Sonstigethe filtrate is evaporated to dryness under reduced pressure

Vorschrift

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]+.

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