Реакция #70909

Уравнение реакции

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

Выход 85.0%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

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

Методика

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).

Источник