反应详情

温度

100 °C

To an acetic acid (10 mL) solution of 6-phenylsulfanyl-pyridine-3-carbaldehyde (583 mg, 2.71 mmol) described in Manufacturing Example 97-1-2 were added nitromethane (734 μL, 13.6 mmol) and ammonium acetate (418 mg, 5.42 mmol), and which was stirred for 4 hours 35 minutes at 100° C. under nitrogen atmosphere. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure. To a dimethyl sulfoxide (10 mL) and acetic acid (1 mL) solution of the residue was added sodium borohydride (205 mg, 5.42 mmol), which was stirred for 55 minutes at room temperature. Sodium hydrogencarbonate and water were added to the reaction mixture at room temperature while cooling appropriately, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane: ethyl acetate=1:1) to obtain the title compound (212 mg, 30%).

1. extractionwhich was then extracted with ethyl acetate
2. customThe organic layer was separated
3. washwashed with saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under a reduced pressure
7. stirringwas stirred for 55 minutes at room temperature
8. temperaturewhile cooling appropriately
9. extractionwhich was then extracted with ethyl acetate
10. customThe organic layer was separated
11. washwashed with water and saturated aqueous sodium chloride
12. dry with materialdried over anhydrous magnesium sulfate
13. filtrationfiltered
14. concentrationThe filtrate was concentrated under a reduced pressure
15. customthe residue was purified by NH silica gel column chromatography (heptane: ethyl acetate=1:1)