反应详情

To a solution of the amine (Step E, 45 mg, 0.15 mmol) and CH2Cl2 (10 mL) was added 4-pyridinecarboxaldehyde (0.04 mL, 0.39 mmol) and NaBH(OAc)3 (95 mg, 0.45 mmol). The reaction was stirred at RT for 7 h then quenched with H2O and extracted with CH2Cl2. The organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give the crude product as an orange oil. The crude product was dissolved in 10 mL CH2Cl2 and stirred with PS-TsNHNH2 resin to remove un-reacted aldehyde. After 1 h, the mixture was filtered through Celite® and concentrated in vacuo. The residue was purified by silica flash chromatography (20-75% EtOAc:hexane) to give the desired product as a light-yellow crystalline solid. MS m/e 385 (M+H)+. Calc'd for C24H24N4O-384.47.

1. customthen quenched with H2O
2. extractionextracted with CH2Cl2
3. washThe organic layer was washed with H2O and brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customto give the crude product as an orange oil
7. customto remove
8. customun-reacted aldehyde
9. waitAfter 1 h
10. filtrationthe mixture was filtered through Celite®
11. concentrationconcentrated in vacuo
12. customThe residue was purified by silica flash chromatography (20-75% EtOAc:hexane)