Réaction #70910

Équation de réaction

4-[1-benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine

1-chloroethyl chloroformate

→

2,6-bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine

Rendement 70.1%

Solvants

dichloroethane

Conditions de réaction

Traitement

1. 1
   Températureto reflux for 3 hours
2. 2
   Concentrationconcentrated under the reduced pressure
3. 3
   workup.ADDITIONMethanol was added to the resultant residue, which
4. 4
   Températurewas then heated
5. 5
   TempératureThe mixture was cooled to room temperature, to which
6. 6
   LavageThe solution was washed twice with the mixed solvent of hexane
7. 7
   Extractionextracted with tert-butyl methyl ether three times
8. 8
   Lavagewhich was then washed with brine
9. 9
   Séchagedried over anhydrous magnesium sulfate
10. 10
    FiltrationAfter the drying agent was filtered off
11. 11
    workup.DISTILLATIONthe solvent was distilled away under the reduced pressure

Mode opératoire

The solution of 4-[1-benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine (1.4 g) and 1-chloroethyl chloroformate (0.905 g) in dichloroethane was heated to reflux for 3 hours. The mixture was cooled to room temperature and then concentrated under the reduced pressure. Methanol was added to the resultant residue, which was then heated with stirring at 60° C. for two hours. The mixture was cooled to room temperature, to which was then added water. The solution was washed twice with the mixed solvent of hexane. The solution was neutralized with sodium hydroxide and then extracted with tert-butyl methyl ether three times. The organic layer was combined, which was then washed with brine and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure to yield 2,6-bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine (0.781 g).

Source