反应详情

To a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzaldehyde (1 eq.) from the previous step in DCM was added cyclopropanamine (2 eq.) and magnesium sulfate (1.5 eq.). The resulting suspension was stirred at rt for 12 h. The insolubles were removed via filtration. Concentration of the filtrate in vacuo afforded the crude imine as a yellow oil. This was then taken up in methanol (0.3 M), and then sodium borohydride (1.5 eq.) was added portionwise at 0° C. over 5 min. The reaction mixture was slowly warmed to rt over 1 h and then stirred at it for 2 h. The reaction was slowly quenched with saturated aqueous NaHCO3 solution, and the resulting mixture was extracted with ether. The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated in vacuo to afford the title compound as a golden, yellow oil.

1. customThe insolubles were removed via filtration
2. customConcentration of the filtrate in vacuo afforded the crude imine as a yellow oil
3. temperatureThe reaction mixture was slowly warmed to rt over 1 h
4. stirringstirred at it for 2 h
5. customThe reaction was slowly quenched with saturated aqueous NaHCO3 solution
6. extractionthe resulting mixture was extracted with ether
7. washThe combined organic extracts were washed with water, brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo