Potassium Hydroxide → HCID 66574520, compound

Participants

Reaction Steps

Potassium hydroxide powder (85% assay, 0.32 g, 0.0049 mol) and 18-crown-6-ether (0.01 g) are added to a solution of 1-{4-[5-(3-chloro-4-cyclopentylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}-4-methoxymethylpiperidine-4-carboxylic acid ethyl ester (0.3 g, 0.00056 mol) in dry toluene (15 mL). The reaction mixture is refluxed for 3 hrs. It is then concentrated under reduced pressure and the residue is acidified to pH˜4-5 with 20% aqueous solution of acetic acid (10 mL). The precipitated solid is filtered, dried and washed with demineralised water (2×10 mL) and acetone (2×5 mL). Solid mass is dissolved in a solution of methanol:dichlromethane:t-butylamine (1:8.9:0.1; 5 mL) and concentrated under reduced pressure to get crude residue which is purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane:t-butylamine, 1:8.9:0.1) to give 1-{4-[5-(3-chloro-4-cyclopentylphenyl)-[1,2,4]-oxadiazol-3-yl]benzyl}-4-methoxymethylpiperidine-4-carboxylic acid.

Provenance & Evidence