Trifluoroacetic acid → 4-((Azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

Participants

Reaction Steps

A solution of 56 g (116.32 mmol) of 4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepane-1-carboxylic acid tert-butyl ester in 150 mL of dichloromethane at 0° C. (ice bath) is treated with trifluoroacetic acid (150 mL, 1.98 mol). The mixture is stirred at room temperature under nitrogen for 2 hours. The reaction mixture is concentrated. The crude product is dissolved with EtOAc (300 mL), washed with a solution 2N—NaOH (2×100 mL) and washed with brine (1×100 mL). The organics are dried (Na2SO4), filtered and concentrated to afford 38 g of the desired compound as a yellow oil (86%). MS (m/e): 381 (M+1).

Provenance & Evidence