反应详情

To a solution of (E)-(2-nitrovinyl)benzene (110 g, 0.738 mol) and TFA (8.42 g, 0.073 mol) in DCM (500 mL) was added N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methan-amine (351.4 g, 1.476 mol) in DCM (500 mL) drop-wise at 0° C. for a period of 30 min. Then the reaction mixture was stirred at room temperature for 48 h. After completion of the reaction, the mixture was concentrated in vacuo, dissolved in water, and extracted into EtOAc (×2, 1.0 L). The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified via flash chromatography (20-80% petroleum ether/EtOAc) to afford (3S and R,4R and S)-1-benzyl-3-nitro-4-phenylpyrrolidine. MS ESI calc'd. For C17H18N2O2 [M+1]+ 283. found 283.

1. customAfter completion of the reaction
2. concentrationthe mixture was concentrated in vacuo
3. dissolutiondissolved in water
4. extractionextracted into EtOAc (×2, 1.0 L)
5. customThe organic layer was separated
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified via flash chromatography (20-80% petroleum ether/EtOAc)