Triethylamine → HCID 66718156, compound

Participants

Reaction Steps

To a solution of (E)-3-(5-fluoropyridin-2-yl)-5-styrylisoxazole-4-carboxylic acid (1.2 g, 3.7 mmol) and triethylamine (0.52 mL, 3.7 mmol) in THF (30 mL) was added dropwise at room temperature a solution of ethyl chloroformate (0.36 mL, 3.7 mmol) in THF (4 mL). After 1 h the triethylamine hydrochloride salt was filtered off and washed with a small amount of THF. The filtrate was added to a solution of sodium borohydride (354 mg, 9.4 mmol) in water (3.5 mL). After stirring for 1 h at 5° C. aqueous sodium hydroxide (1 M, 11 mL) was added. Extraction with ethyl acetate, drying over sodium sulfate, filtering and evaporation of the solvent followed by trituration with diisopropylether afforded the title compound (895 mg, 81%) as a white solid after purification by chromatography (SiO2, DCM). MS: m/e=297.2 [M+H]+.

Provenance & Evidence