反应详情

温度

0 °C

To a solution of benzyl rel-(3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxypyrrolidine-1-carboxylate (1 g, 2.97 mmol) in dry THF (10 mL) at 0° C. was added NaH (475 mg, 11.88 mmol). The reaction mixture was stirred at 0° C. for 1 h. Allyl bromide (1.08 g, 8.92 mmol) was added to the reaction mixture dropwise. The reaction mixture was stirred at 0° C. for 2 h and room temperature for 1 h. The reaction was quenched by adding MeOH (5 mL) and was concentrated under reduced pressure to remove most of the solvent. Then water (15 mL) was added to the reaction mixture. EtOAc (15 mL×3) was added to extract the product. The organic phases were combined, dried over MgSO4, filtered, concentrated and subjected to column chromatography (EtOAc:hexanes, 1:3 to 1:1) as the eluent to give benzyl rel-(3R,4R)-3-(allyloxy)-4-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate (806.2 mg, 72%).

1. stirringThe reaction mixture was stirred at 0° C. for 2 h and room temperature for 1 h
2. customThe reaction was quenched
3. additionby adding MeOH (5 mL)
4. concentrationwas concentrated under reduced pressure
5. customto remove most of the solvent
6. additionThen water (15 mL) was added to the reaction mixture
7. additionEtOAc (15 mL×3) was added
8. extractionto extract the product
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated