反应详情

Nitromethane (4.33 mL) was added to a solution of trans-2-pentenal (2.27 g) and (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine (Org. Lett., 2007, vol. 9, p. 5307) (920 mg) in methanol (54 mL) with stirring at room temperature. The mixture was stirred at room temperature for 4 days. Then, trimethyl orthoformate (17.7 mL) and p-toluenesulfonic acid monohydrate (1.03 g) were added to the reaction solution, and the mixture was further stirred overnight. The reaction solution was concentrated, and a saturated aqueous solution of sodium bicarbonate was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and then dried over anhydrous sodium sulfate. Filtration and concentration under reduced pressure were performed to obtain the title compound (4.81 g).

1. stirringThe mixture was stirred at room temperature for 4 days
2. concentrationThe reaction solution was concentrated
3. additiona saturated aqueous solution of sodium bicarbonate was added to the residue
4. extractionfollowed by extraction with ethyl acetate
5. washThe organic layer was washed with saturated sodium chloride solution
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationFiltration and concentration under reduced pressure