Putrescine → HCID 86672881, compound

Participants

Reaction Steps

A solution of 1,4-diaminobutane (88.2 grams) in 100 mL ethanol was added to ice cooled diethyl oxalate (1461 grams) in ethanol (1400 mL) over 40 minutes, maintaining the internal temperature below 8° C. The reaction was allowed to gradually warm to ambient temperature, and after 48 hours, the crude solids (168 grams) were collected by filtration. The product (22 grams) was purified by flash column chromatography (EtOAc as the eluent) and then boiled in MTBE (200 mL) to obtain butylene-bis-oxamic acid ethyl ester as a white solid having a melting point in the range of 114.4 to 116.4° C. 1H NMR (CDCl3, 300 MHz) δ 7.23 (brs, 2H), 4.33 (q, J=7.1 Hz, 4H), 3.36 (q, J=6.5 Hz, 4H), 1.64-1.59 (m, 4H), 1.36 (t, J=7.2 Hz, 6H).

Provenance & Evidence