Réaction #1269844

Équation de réaction

diethyl azodicarboxylate

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

triphenylphosphine

→

product

Rendement 92.0%

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

Rendement 92.0%

Solvants

toluene

THF

Conditions de réaction

Traitement

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

Mode opératoire

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]+.

Source