Reaktion #70910

Reaktionsgleichung

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

Ausbeute 70.1%

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 3 hours
2. 2
   Einengenconcentrated under the reduced pressure
3. 3
   workup.ADDITIONMethanol was added to the resultant residue, which
4. 4
   Temperaturwas then heated
5. 5
   TemperaturThe mixture was cooled to room temperature, to which
6. 6
   WaschenThe solution was washed twice with the mixed solvent of hexane
7. 7
   Extraktionextracted with tert-butyl methyl ether three times
8. 8
   Waschenwhich was then washed with brine
9. 9
   Trocknendried 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

Vorschrift

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).

Quelle