Benzyl Bromide → Tert-butyl (4-benzyl-2-methoxypyridin-3-yl)carbamate

Temperature

0 °C

To a solution of tert-butyl (2-methoxypyridin-3-yl)carbamate (25.1 g) and N,N,N′,N′-tetramethylethane-1,2-diamine (40.6 mL) in diethyl ether (374 mL) was added 1.6M n-butyllithium hexane solution (168 mL) at −78° C., and the mixture was stirred under argon atmosphere at 0° C. for 1 hr. To the reaction mixture was added benzyl bromide (24.9 g) at −78° C., and the mixture was stirred under argon atmosphere at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane), and crystallized from ethyl acetate and hexane to give the title compound (25.4 g).

1. stirringthe mixture was stirred under argon atmosphere at room temperature for 4 hr
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)
7. customcrystallized from ethyl acetate and hexane

ORD record

ord-b8ce2941a1e843679df7c70fa0c3bb9f

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371320B2