反应详情

A slurry of ethyl 3-benzyl-2,4-dimethylquinoline-6-carboxylate (99.5 mg, 0.312 mmol, Intermediate 34: step b) and N,O-dimethylhydroxylamine.HCl (42.2 mg, 0.433 mmol) in THF (1 mL) was stirred at 0° C. under argon while iPrMgCl (2.01 M in THF, 0.43 mL, 0.864 mmol) was added dropwise. The resulting dark solution was stirred at 0° C. overnight while the ice bath expired. It was then quenched with 5 M aqueous NH4Cl (4 mL) and extracted with EtOAc (2×3 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated, and the residue was flash chromatographed with a heptane to 100% EtOAc gradient to yield the title compound as an amber oil.

1. additionwas added dropwise
2. customIt was then quenched with 5 M aqueous NH4Cl (4 mL)
3. extractionextracted with EtOAc (2×3 mL)
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customchromatographed with a heptane to 100% EtOAc gradient