Borane;tetrahydrofuran → HCID 57588493, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)-2-oxoethylcarbamate (500 mg, 1.08 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL) and cooled to 0° C. Borane-tetrahydrofuran complex (1M soln in THF, 10.8 mL, 10.8 mmol) was added dropwise to the cool solution. The reaction mixture was allowed to stir while slowly warming to room temperature for 5 h. The reaction was quenched with 1N hydrochloric acid (25 mL) and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to yield tert-butyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)ethylcarbamate as a white solid. The product was carried forward without further purification. 1H NMR (CDCl3): 7.98 (s, 1H), 7.55-7.50 (m, 2H), 7.48-7.35 (m, 4H), 6.48 (s, 1H), 5.18 (br s, 1H), 4.00 (m, 2H), 3.58 (m, 2H), 1.48 ppm (s, 9H).

Provenance & Evidence