Triethylamine → (2S)-2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propan-1-ol

A solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (5.0 g, 22.6 mmol) in 50 mL of dry DMF was cooled to 0° C. under an atmosphere of N2. Triethylamine (6.3 mL, 45.2 mmol) and L-alaninol (2.1 mL, 27.1 mmol) were added sequentially. After approximately 15 minutes, the reaction was allowed to warm to ambient temperature, and then heated to 35° C. for 3 days. The reaction mixture was concentrated under reduced pressure to give an orange-brown solid. The resulting solid was partitioned between 50 mL of ethyl acetate and 50 mL of H2O. The layers were separated and the organic portion was washed sequentially with H2O and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 40-60% ethyl acetate/hexanes) afforded (2S)-2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propan-1-ol (3.62 g) as an orange solid.

1. temperatureheated to 35° C. for 3 days
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customto give an orange-brown solid
4. customThe resulting solid was partitioned between 50 mL of ethyl acetate and 50 mL of H2O
5. customThe layers were separated
6. washthe organic portion was washed sequentially with H2O and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-95828df36af543af938139b8e4ac7f63

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943609B2