反应详情

1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (35 mg, 0.187 mmol), sodium acetate (19.94 mg, 0.243 mmol), and 2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethanaminium chloride (45.2 mg, 0.187 mmol) were combined in 1,2 dichloroethane (2 ml). Acetic acid (0.021 ml, 0.374 mmol) and sodium triacetoxyborohydride (119 mg, 0.561 mmol) were added and the reaction stirred for 20 hours. The mixture was partitioned between CH2Cl2 and satd. bicarb and the aqueous portion was extracted 3×CH2Cl2. The organic portion was dried (Na2SO4) and concentrated in vacuo. The resulting material was purified by reversed-phase chromatography (10-60% ACN in water (with 2 ml/l NH4OH) over 20 min at 20 ml/min, 20×100 mm Phenomenex Gemini C18 column). Desired fractions were concentrated in vacuo. 50.5 mg, 73%.

1. customThe mixture was partitioned between CH2Cl2 and satd
2. extractionbicarb and the aqueous portion was extracted 3×CH2Cl2
3. dry with materialThe organic portion was dried (Na2SO4)
4. concentrationconcentrated in vacuo
5. customThe resulting material was purified by reversed-phase chromatography (10-60% ACN in water (with 2 ml/l NH4OH) over 20 min at 20 ml/min, 20×100 mm Phenomenex Gemini C18 column)
6. concentrationDesired fractions were concentrated in vacuo