反应详情

温度

0 °C

A 1.8 M solution of lithium diisopropylamide in tetrahydrofuran (4.10 mL) was added dropwise to a solution of (3S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester in tetrahydrofuran in a nitrogen atmosphere at −73° C. over 10 minutes. After stirring at the same temperature for 15 minutes, a solution of N-fluorobenzenesulfonimide (2.63 g, 8.33 mmol) in tetrahydrofuran (18 mL) was added dropwise over 15 minutes. After stirring at the same temperature for 30 minutes, a saturated ammonium chloride solution (20 mL) was added, and the mixture was heated to 0° C. The reaction solution was poured into a mixture of ethyl acetate (100 mL) and 1 mol/mL hydrochloric acid (50 mL), followed by extraction with ethyl acetate (200 mL). The organic layer was sequentially washed with a saturated sodium bicarbonate solution (50 mL) and brine (50 mL×2) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Dichloromethane was added to the resulting residue to prepare a slurry, and the solid was removed by filtration. The filtrate was concentrated, and the resulting solid was removed by filtration. The filtrate was further concentrated to give 3.44 g of the crude title compound as a pale yellow oil. The resulting crude was used for the next reaction without further purification.

1. stirringAfter stirring at the same temperature for 30 minutes
2. extractionfollowed by extraction with ethyl acetate (200 mL)
3. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution (50 mL) and brine (50 mL×2)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationAfter filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. additionDichloromethane was added to the resulting residue
8. customto prepare a slurry
9. customthe solid was removed by filtration
10. concentrationThe filtrate was concentrated
11. customthe resulting solid was removed by filtration
12. concentrationThe filtrate was further concentrated