反应详情

温度

-10 °C

Add n-butyllithium (3.30 mL, 8.25 mmol, 2.5 M in hexanes) to a solution of 2,2,6,6-tetramethylpiperidine (1.40 mL, 8.18 mmol) in tetrahydrofuran (THF) (30 mL) at −78° C. over 2 min. Stir 5 min, then warm to −10° C. and stir 5 min, then cool to −78° C. Add N-tert-butoxycarbonylpyrrole (1.37 mL, 8.25 mmol) in THF (1.6 mL) over 3 min. Stir 30 min and add 2-(S)-[bis-(2-methylbenzyl)-amino]-3-(3,5-difluorophenyl)-propionaldehyde (2.96 g, 7.44 mmol) in THF (15 mL) over 5 min. Stir 60 min at −78° C., warm to 0° C. and stir 60 min. Cool −78° C. and quench with saturated aqueous ammonium chloride solution. Extract with ethyl acetate, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and dichloromethane) to give the title compound as a foam (0.416 g, 10%).

1. stirringstir 5 min
2. temperaturecool to −78° C
3. stirringStir 30 min
4. stirringStir 60 min at −78° C.
5. temperaturewarm to 0° C.
6. stirringstir 60 min
7. temperatureCool −78° C.
8. customquench with saturated aqueous ammonium chloride solution
9. extractionExtract with ethyl acetate
10. dry with materialdry (magnesium sulfate)
11. concentrationconcentrate
12. custompurify
13. wash(silica gel chromatography, eluting with hexanes and dichloromethane)