反应详情

温度

-78 °C

To a solution of intermediate (2S,3S)—N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-formylpyrrolidine (4.7 g, 14.26 mmol) in THF (70 mL) at −78° C. was added dropwise MeMgBr (3.0 M in THF, 23.8 mmol). The reaction was stirred at −78° C. for 3 h and TLC (20% EtOAc/hexane) showed complete reaction. The reaction was quenched by the addition of HOAc (5.0 mL) at −78° C., warmed to rt and diluted with EtOAc (20 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with saturated NaHCO3 solution and brine, dried (MgSO4), filtered and concentrated to give the crude product. Purification by flash chromatography (120 g ISCO silica gel column, 0-30% EtOAc/hexane) provided 80A-a (760 mg) and 80A-b (1.54 g) as colorless oil. 80A-a: For (20% EtOAc/hexane) 0.29. 80A-b: For (20% EtOAc/hexane) 0.25.

1. customreaction
2. customThe reaction was quenched by the addition of HOAc (5.0 mL) at −78° C.
3. temperaturewarmed to rt
4. additiondiluted with EtOAc (20 mL)
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with EtOAc (2×30 mL)
7. washThe combined organic layers were washed with saturated NaHCO3 solution and brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customto give the crude product
12. customPurification by flash chromatography (120 g ISCO silica gel column, 0-30% EtOAc/hexane)