Sodium borohydride → 1-(2-Aminopyridin-4-yl)ethanol

To a mixture of 1-(2-aminopyridin-4-yl)ethanone (21) (168 mg, 1.234 mmol) in MeOH (10 mL), under nitrogen at 0° C., was added sodium borohydride (46.7 mg, 1.234 mmol). The resulting reaction mixture was stirred at RT for 2 hr, and then the solvents were removed under reduced pressure. The residue was taken up into EtOAc (25 mL), and extracted with saturated aq NaHCO3 solution (30 mL) and the layers separated. The aqueous layer was extracted with EtOAc (20 mL×2), and the combined organic extracts were washed with brine (30 mL), dried and the solvents removed under reduced pressure, to give 1-(2-aminopyridin-4-yl)ethanol (22) (77 mg, 45%) as a yellow oil: m/z 139 (M+H)+ (ES+).

1. customThe resulting reaction mixture
2. customthe solvents were removed under reduced pressure
3. extractionextracted with saturated aq NaHCO3 solution (30 mL)
4. customthe layers separated
5. extractionThe aqueous layer was extracted with EtOAc (20 mL×2)
6. washthe combined organic extracts were washed with brine (30 mL)
7. customdried
8. customthe solvents removed under reduced pressure

ORD record

ord-85bea427b38c47cfae92a61c53aae763

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293748B2