CarbaMic acid, N-[(1R)-1-[3-[6-(trifluoroMethyl)-1H-benziMidazol-2-yl]-5-isoxazolyl]ethyl]-, 1,1-diMethylethyl ester → 5-IsoxazoleMethanaMine, α-Methyl-3-[6-(trifluoroMethyl)-1H-benziMidazol-2-yl]-, (αR)-

Participants

Reaction Steps

A mixture of (R)-tert-butyl 1-(3-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)isoxazol-5-yl)ethylcarbamate (86.5 g, 0.22 mol) in TFA (300 mL) was stirred at RT for 2 hr. The reaction mixture was concentrated in vacuo and re-dissolved in ethyl acetate. The ethyl acetate solution was washed with K2CO3 and water, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography to afford compound Na, (R)-1-(3-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)isoxazol-5-yl)ethanamine (30.2 g, 46.7%). 1H NMR (DMSO-d6) δ 7.98 (s, 1H), 7.78 (d, 1 H), 7.56 (d, 1H), 6.94 (s, 1H), 4.16 (q, 1H), 1.36 (d, 3H).

Provenance & Evidence