Trifluoroacetic acid → (2R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-amine

Participants

Reaction Steps

To a solution of tert-butyl(R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-ylcarbamate (0.089 g, 0.20 mmol) in 5 mL of DCM was added 1 mL of TFA. After 30 minutes, the solvent was removed by rotary evaporation. The residue was taken up in 2 N NH3/MeOH to free base the amine. Concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 10% MeOH/DCM) afforded (2R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-amine (0.015 g, 22% yield) as a brown solid. MS m/z: 344 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.46 (s, 1H), 8.58-8.55 (m, 1H), 8.48 (s, 1H), 8.35-8.25 (m, 2H), 8.12 (d, J=6.2 Hz, 1H), 7.40-7.27 (m, 5H), 6.79 (s, 1H), 3.61-3.50 (m, 2H), 3.19-2.94 (m, 3H), 2.16-2.03 (m, 2H).

Provenance & Evidence