Hydrochloric Acid → 4-{[(2S)-2-fluoropropyl]oxy}pyridine

A solution of 1.5 g of 4-hydroxypyridine, 7.6 g of cyanomethylenetributylphosphorane, and 1.4 g of (2S)-2-fluoro-1-propanol in 20 mL of toluene was stirred at 105° C. overnight. To the reaction mixture were added 1 M hydrochloric acid and ethyl acetate, and the organic layer was separated. The aqueous layer was adjusted to pH 11 by the addition of a 1 M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 2.2 g of 4-{[(2S)-2-fluoropropyl]oxy}pyridine.

1. customthe organic layer was separated
2. additionThe aqueous layer was adjusted to pH 11 by the addition of a 1 M aqueous sodium hydroxide solution
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

ORD-Eintrag

ord-7a62bb2315da4ddd9ab4f2c528883a6b

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822448B2