Ammonium Chloride → [6-(Dimethoxymethyl)-2-methoxypyridin-3-yl]methanol

Diisopropylethylamine (4.56 mL) and Bop reagent (registered trademark) (10 g) were added to a solution of 6-(dimethoxymethyl)-2-methoxypyridine-3-carboxylic acid (4.1 g) in tetrahydrofuran (40 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0° C. and sodium borohydride (2.72 g) was added, followed by stirring at room temperature overnight. The reaction solution was poured into a saturated ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1) to give [6-(dimethoxymethyl)-2-methoxypyridin-3-yl]methanol (2.3 g, 60%) as a colorless oil.

1. temperaturecooling
2. temperatureThe reaction solution was cooled to 0° C.
3. stirringby stirring at room temperature overnight
4. extractionfollowed by extraction with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customThe solvent was then evaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1)

ORD record

ord-eb7d843b3a84483db93c3e41c8d87652

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822503B2