반응 #70909

반응 방정식

2,6-bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine

N-benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine

→

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

수율 85.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도while cooling with ice
2. 2
   workup.ADDITIONOn completion of the dropwise addition
3. 3
   세척The mixture was washed with saturated sodium bicarbonate water
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   여과After the drying agent was filtered off
6. 6
   workup.DISTILLATIONthe solvent was distilled away under the reduced pressure
7. 7
   기타the residue was then purified by silica gel chromatography

실험 절차

To the solution of 2,6-bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine (1.25 g) and N-benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (5.0 g) in dichloromethane was added dropwise the solution of trifluoroacetic acid (0.038 g) in dichloromethane while cooling with ice. On completion of the dropwise addition, the mixture was warmed to room temperature and stirred over night. The mixture was washed with saturated sodium bicarbonate water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield 4-[1-benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine (1.52 g). 1H-NMR (CDCl3) δ: 2.23-2.29 (1H, m), 2.65-2.69 (2H, m), 2.96 (1H, d), 3.05-3.15 (2H, m), 3.58 (1H, d), 3.82 (1H, d), 7.26-7.37 (5H, m), 8.00 (2H, s).

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