Methyl iodide → Ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylate

Temperature

80 °C

To a solution of ethyl isonicotinate (151 g) in ethyl acetate (1000 mL) was added methyl iodide (126 mL), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was cooled, and the orange precipitate was collected by filtration. The precipitate was suspended in ethanol (1000 mL), sodium borohydride (37.8 g) was added with cooling at −40° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and ethanol was evaporated under reduced pressure. The resultant product was extracted with ethyl acetate-tetrahydrofuran, the organic layer was dried, and the solvent was evaporated under reduced pressure. The residue was distilled under reduced pressure to give ethyl 1-methyl-1,2,3,6-tetrahydropyridine-4-carboxylate (85.8 g, 51%) as a pale yellow oil.

1. temperatureThe reaction mixture was cooled
2. filtrationthe orange precipitate was collected by filtration
3. additionsodium borohydride (37.8 g) was added
4. temperaturewith cooling at −40° C.
5. stirringthe mixture was stirred at room temperature for 2 hr
6. additionThe reaction mixture was poured into water, and ethanol
7. customwas evaporated under reduced pressure
8. extractionThe resultant product was extracted with ethyl acetate-tetrahydrofuran
9. customthe organic layer was dried
10. customthe solvent was evaporated under reduced pressure
11. distillationThe residue was distilled under reduced pressure

ORD record

ord-1262771a08fb4a4b9ffdc851069892bb

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470816B2