反应详情

温度

-78 °C

1-(4-methoxybenzyl)piperidine-2,6-dione (8.99 g, 38.5 mmol) was dissolved in Toluene (Volume: 128 ml) and cooled to −78° C. L-Selectride (42.4 ml, 42.4 mmol) was added dropwise and the mixture agitated for 1 h. After 1 h, thick slurry along with precipitate observed. Reaction mixture was briefly pulled outside cooling bath to homogenize the mixture. Then DMAP (0.047 g, 0.385 mmol) was added in one portion and then DIEA (38.4 ml, 220 mmol) was added and then TFAA (6.53 ml, 46.2 mmol) was added. Then the cooling flask was removed and the mixture agitated at room temperature for 2 h and then quenched with water and the product extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford crude residue which was purified by flash chromatography to afford 7.66 g of the desired product as a yellow syrup. LCMS (m/z): (MH+), 234.2, 0.73 min.

1. waitAfter 1 h
2. customReaction mixture
3. temperatureoutside cooling bath
4. stirringto homogenize the mixture
5. customThen the cooling flask was removed
6. stirringthe mixture agitated at room temperature for 2 h
7. customquenched with water
8. extractionthe product extracted with EtOAc
9. dry with materialThe combined organic layer was dried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto afford crude residue which
13. customwas purified by flash chromatography