2-Aminopyridine → Methyl 5-(pyridin-2-ylamino)pentanoate

To a solution of methyl 5-oxopentanoate (3.0 g, 23 mmol) in methylene chloride (75 mL) was added 2-aminopyridine (2.38 g, 25.3 mmol). The mixture was stirred at room temperature for 30 minutes. Then, the sodium triacetoxy borohydride (7.31 g, 34.5 mmol) was added and the mixture was stirred at room temperature for 4.5 hours. A saturated solution of sodium bicarbonate (40 mL) was added and the reaction mixture was extracted with ether (4×30 mL). The organic layer was washed with 0.1 N NaOH, water (2×40 mL), dried (MgSO4) and concentrated. The residue was purified by flash chromatography 1:1 (Acetone:methylene chloride) to obtain 2.31 g (48%) of the product. 1H NMR (CDCl3) 8.09-8.06 (m, 1H), 7.42-7.38 (m, 1H), 6.59-6.52 (m, 1H), 6.37 (d, J=9 Hz, 1H), 4.52 (br s, 1H), 3.68 (s, 3H), 3.29 (q, J=6 Hz, 2H), 2.40-2.31 (m, 2H), 1.8-1.61 (m, 4H).

1. stirringthe mixture was stirred at room temperature for 4.5 hours
2. extractionthe reaction mixture was extracted with ether (4×30 mL)
3. washThe organic layer was washed with 0.1 N NaOH, water (2×40 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe residue was purified by flash chromatography 1:1 (Acetone:methylene chloride)

ORD record

ord-fb47ad7f6ad14cdbaf605ba43793df56

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933304B2