Trifluoroacetic acid → HCID 71449747, compound

Participants

Reaction Steps

Compound 17 (312 mg, 0.7 mmol) was dissolved in anhydrous CH2Cl2 (3 mL) and cooled in an ice-water bath. TFA (3 mL) was added in 30 min. After stirring at room temperature for 1 hr, the mixture was poured into a cold solution of NH4OH in water (1:1). The mixture was then extracted with CH2Cl2. The organic phase was washed with brine, then dried over anhydrous Na2SO4 and evaporated to dryness. After flash chromatography on a silica gel column with CH2Cl2-MeOH, the free base was isolated as a clear oil (242 mg, 99%). 1H NMR (CDCl3): δ (ppm) 1.5-1.7 (m, 5H), 1.8-1.9 (m, 1H), 2.87 (dd, 1H, J=5.1, 9.0 Hz), 3.11 (s, 3H), 3.65 (br s, 1H), 3.84 (m, 1H), 7.7-7.8 (m, 2H), 8.0-8.05 (m, 2H), 8.09 (dd, 1H, J=2.4, 3.6 Hz), 8.15 (m, 1H). 13C NMR (CDCl3): δ (ppm) 29.6, 30.5, 31.7, 40.8, 44.6, 44.9, 56.8, 63.2, 121.6 (d, J=112.5 Hz), 128.0, 130.2 (d, J=12.3 Hz), 140.3 (d, J=14.7 Hz), 141.3 (d, J=18.6 Hz), 146.6 (d, J=57.6 Hz), 157.6, 160.8.

Provenance & Evidence