Ethyl 4-piperidinecarboxylate → HCID 23438700, compound

Temperature

190 °C

5-Bromo-2-fluoropyridine A-5 (0.31 mL, 3.0 mmol) and ethyl piperidine-4-carboxylate (1.39 mL, 9.0 mmol) were dissolved in anhydrous pyridine (2.0 mL) at room temperature under an argon atmosphere, in a 10 mL microwave reactor vial. The reaction mixture was sealed and heated at 190° C. for 60 mins under microwave irradiation, then successively cooled to room temperature, diluted with methylene chloride (60 mL), quenched with a 1 N aqueous solution of hydrogen chloride (40 mL) and decanted. The aqueous layer was extracted with methylene chloride (2×100 mL); the combined extracts were sequentially washed with water (70 mL), brine (70 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient) to give ethyl 1-(5-bromopyridin-2-yl)piperidine-4-carboxylate A-14 (935.0 mg, Yield=99%). MS (ESI), [M+1]+ 313, 315.

1. customThe reaction mixture was sealed
2. temperaturesuccessively cooled to room temperature
3. customquenched with a 1 N aqueous solution of hydrogen chloride (40 mL)
4. customdecanted
5. extractionThe aqueous layer was extracted with methylene chloride (2×100 mL)
6. washthe combined extracts were sequentially washed with water (70 mL), brine (70 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated to dryness under reduced pressure
10. customThe crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient)

ORD record

ord-55014f8eb9f746aba4cc2b587d505674

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637507B2