Reacción #1269844

Ecuación de reacción

diethyl azodicarboxylate

2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

triphenylphosphine

→

product

Rendimiento 92.0%

(3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one

Rendimiento 92.0%

Disolventes

toluene

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSolvent is removed under vacuum
2. 2
   workup.ADDITIONthe residue is treated with 0.02 N HCl (40 mL)
3. 3
   FiltraciónThe precipitate is filtered off
4. 4
   Lavadothe filtrate is washed with CH2Cl2
5. 5
   OtroThe aqueous phase is evaporated to dryness under high vacuum

Procedimiento

To a solution of 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one (130 mg, 0.62 mmol) in anhydrous THF (2 mL) is added triphenylphosphine (163 mg, 0.62 mmol). Five minutes later, diethyl azodicarboxylate (DEAD, 0.45 mL, 0.93 mmol) in toluene is added dropwise. The mixture is stirred at room temperature for 2 hours. Solvent is removed under vacuum, the residue is treated with 0.02 N HCl (40 mL). The precipitate is filtered off, and the filtrate is washed with CH2Cl2. The aqueous phase is evaporated to dryness under high vacuum to give product as solids (108 mg, yield 92%), which is used for the next reaction without further purification. MS (ESI) m/z 192.1 [M+H]+.

Fuente