反应详情

To a methylene chloride (2 mL) solution of (E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-5-oxovaleric acid ethyl ester (162 mg), (S)-(−)-alpha-methylbenzylamine (183 μL), acetic acid (1.0 mL) and sodium triacetoxy borohydride (120 mg) were added one by one. After agitating reaction solution at room temperature overnight, a saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in acetic acid (2 mL), and heat-refluxing of the reaction solution was carried out overnight. After cooling reaction solution to 0° C., neutralized with a saturated sodium bicarbonate water, ethyl acetate was added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate=1:1->ethyl acetate: ethanol=10:1), and 13.7 mg of the title compound was obtained. The physical properties of the compound are as follows.

1. customreaction solution at room temperature overnight
2. customthe organic layer was partitioned
3. washAfter the obtained organic layer was washed with a saturated saline solution, it
4. dry with materialwas dried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe obtained residue was dissolved in acetic acid (2 mL)
7. temperatureheat-refluxing of the reaction solution
8. temperatureAfter cooling
9. customreaction solution to 0° C.
10. additionwas added to the reaction solution
11. customthe organic layer was partitioned
12. washAfter the obtained organic layer was washed with a saturated saline solution, it
13. dry with materialwas dried over anhydrous magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate=1:1->ethyl acetate: ethanol=10:1)