反应详情

To a stirred solution of 2-[4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]-2-oxo-acetic acid ethyl ester (5.3 mmol, 2.0 g) in methanol (55 mL) was added hydroxylamine hydrochloride (21.2 mmol, 1.5 g) followed by potassium hydroxide/methanol solution (5M; 5.3 mL) dropwise at room temperature. A white solid precipitated out of solution as this reaction stirred overnight. The reaction mixture was diluted with H2O (250 mL), acidified with 1N HCl (60 mL) and extracted with EtOAc (2×500 mL). Each organic phase was washed with H2O (250 mL) and the combined organics were dried (Na2SO4) and concentrated in vacuo to give a tan solid. The residue was purified by flash chromatography (SiO2 : 1) 80% EtOAc/hexane, 2) EtOAc) to afford the title compound as a white solid, mp=123.5°-124° C. (2.5 mmol, 0.920 g, 48%).

1. customA white solid precipitated out of solution as this reaction
2. additionThe reaction mixture was diluted with H2O (250 mL)
3. extractionextracted with EtOAc (2×500 mL)
4. washEach organic phase was washed with H2O (250 mL)
5. dry with materialthe combined organics were dried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customto give a tan solid
8. customThe residue was purified by flash chromatography (SiO2 : 1) 80% EtOAc/hexane, 2) EtOAc)