Formaldehyde → HCID 54234832, compound

Participants

Reaction Steps

To a solution of 2-{1-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-malonic acid monoethyl ester (712 mg, 1.95 mmol) in THF (6.5 mL) at 0° C. formaldehyde (37% in water, 0.3 mL) was added within 5 min. Stirring was continued for 10 min, then piperidine (0.26 mL, 2.63 mmol) was added dropwise within 10 min. The mixture was allowed to warm up overnight to room temperature. After 14 h the mixture was concentrated under reduced pressure to one third of its volume, then ether and water were added (15 mL each). After 2 min vigorous stirring the layers were separated, the aqueous was extracted with ether and the combined organic layers were washed with water, 4% citric acid, water and brine. Drying and concentration under reduced pressure gave 2-{1-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-acrylic acid ethyl ester (550 mg, 85%) as a colourless solid.

Provenance & Evidence