反应详情

温度

-78 °C

A mixture of tert-butyl 4-cyanopiperidine-1-carboxylate (220 mg, 1.05 mmol) and 2-fluoropyridine (0.094 mL, 1.10 mmol) was dissolved in 5.2 mL of THF. The reaction was purged with a stream of nitrogen and cooled to −78° C. To this reaction was added sodium bis(trimethylsilyl)amide (1.0 M in THF, 1.47 mL, 1.47 mmol), which was stirred for 1 h. The reaction was warmed to ambient temperature, stirred for 1 hour, and quenched with a saturated ammonium chloride solution. The mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, concentrated, and subjected to silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to provide tert-butyl 4-cyano-4-pyridin-2-ylpiperidine-1-carboxylate.

1. customThe reaction was purged with a stream of nitrogen
2. temperatureThe reaction was warmed to ambient temperature
3. stirringstirred for 1 hour
4. customquenched with a saturated ammonium chloride solution
5. extractionThe mixture was extracted with dichloromethane (3×10 mL)
6. dry with materialThe combined organic extracts were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. washeluting with 0-20% ethyl acetate in hexanes