Hydrochloric Acid → HCID 45792670, compound

Participants

Reaction Steps

Glutaraldehyde (36.5 mL, 95 mmol) and 1,3-acetonedicarboxylic acid (10 g, 65 mmol) were suspended in water (100 mL) and stirred by a mechanical stirrer under argon for 30 min. To the yellow solution cyclopropylamine (3.5 mL, 50 mmol) were added in one portion whereby a slightly exothermic reaction occurred and a gas evolved. The reaction mixture was stirred at 23° C. overnight. The reaction mixture was acidified with 3 N Hydrochloride solution until pH<2, then extracted with dichloromethane. The water layer was now adjusted with 3 N NaOH to pH 8 and extracted three times with dichloromethane, the organic layers were combined, dried over MgSO4, filtered and the solvents were evaporated. Purification of the crude product by flash chromatography with n-heptane and ethyl acetate gave the title compound as a white solid (940 mg, 11%); MS: m/e=180.2 (M+H+).

Provenance & Evidence