Hydroxyamine hydrochloride → HCID 15295468, compound

Participants

Reaction Steps

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%).

Provenance & Evidence