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 0.1N 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 0.1N 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-b113cb4b29f7403fb9918bdbbd896ab2

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119098B2