反应详情

To a solution of 4-(2-cyclopropyl-1,3-oxazol-4-yl)benzaldehyde (0.318 g, 1.49 mmol) in MeOH (5 ml) was added tyramine (0.215 g, 1.57 mmol) and trimethylorthoformate (1.2 mL, 10.97 mmol). The resulting solid was redissolved in THF (3 ml) and allowed to stir for 12 h. Sodium borohydride (0.15 g, 3.94 mmol) was added and the mixture was stirred an additional 2 h. The reaction mixture was concentrated and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with MgSO4, and concentrated in vacuo. The crude material was purified by flash chromatography (MeOH/CH2Cl2, 5:95 to 10:90) to yield 4-(2-{[4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]amino}ethyl)phenol as a white solid (0.43 g, 85%).

1. stirringthe mixture was stirred an additional 2 h
2. concentrationThe reaction mixture was concentrated
3. custompartitioned between EtOAc and water
4. extractionThe aqueous phase was extracted with EtOAc
5. washthe combined organic phases were washed with brine
6. dry with materialdried with MgSO4
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by flash chromatography (MeOH/CH2Cl2, 5:95 to 10:90)