تفاعل #70909

معادلة التفاعل

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

المردود 85.0%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر