Formaldehyde → HCID 54506217, compound

Participants

Reaction Steps

Diethylamine (3.67 ml, 3.67 mmol) was added dropwise followed by water (2.5 ml) and CH2Cl2 (2.5 ml) to a mixture of 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.40 g, 3.64 mmol) and 37% aq. solution of formaldehyde (0.29 ml, 3.75 mmol) in CH2Cl2 (2 ml) at 0° C. The mixture was stirred for 20 h at room temperature and then poured onto ice-water and extracted with methylene chloride. The organic layer was washed with 5% NaHCO3, dried and concentrated under reduced pressure. Flash chromatography (1-2.5% methanol in CH2Cl2) yielded 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-acrylic acid ethyl ester 0.81 g (65%).

Provenance & Evidence