Cyclopropanemethanamine → HCID 68851544, compound

Participants

Reaction Steps

To a solution of 3-(5-methyl-3-phenyl-isoxazol-4-ylethynyl)-benzoic acid (250 mg; 0.82 mmol) in N,N-dimethylformamide (4.8 mL) was added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (318 mg, 0.99 mmol) at 0° C. After stirring for 15 min at this temperature, aminomethylcyclopropane (86 μl, 0.99 mmol) and N-ethyldiisopropylamine (0.85 mL, 4.94 mmol) were added and the reaction mixture was allowed to warm to ambient temperature. After 1.75 h stirring at ambient temperature, it was extracted with dichloromethane (300 mL) and aqueous sodium carbonate (2 M, 75 mL). The combined organic layers were washed with brine (75 mL), dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 0:100) afforded the title compound (254 mg, 87%) as a white solid. MS: m/e=357.1 [M+H]+.

Provenance & Evidence