Hydrochloric Acid → HCID 67314388, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-fluoro-1,3-dihydro-indol-2-one (150 mg, 1.0 mmol) in THF (5 mL) at room temperature is treated with lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 2.0 mL, 2.0 mmol) and stirred for 10 min. A solution of 1-[3-(5-oxo-5,7-dihydro-furo[3,4-b]pyridin-2-yl)-propyl]-piperidine-4-carboxylic acid ethyl ester (110 mg, 1 equiv) in anhydrous THF (2 mL) is added. The reaction mixture is stirred at room temperature for 3 h. The reaction mixture is poured into aqueous 2N HCl solution (10 mL) with stirring. Then it is heated at 60° C. for 2 h. To the mixture is then added ice water (100 mL) followed by the careful addition of saturated aqueous NaHCO3 to adjust the pH to 8. The foamy suspension is filtered and a greenish yellow solid is obtained. This material is purified by column chromatography to give the title compound as a yellow solid (48 mg, 33%).

Provenance & Evidence