Trifluoroacetic acid → HCID 44404226, compound

Participants

Reaction Steps

Compound 16 (275 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 (200 mg, 93%). 1H NMR (CDCl3): δ (ppm) 1.5-1.7 (m, 5H), 1.8-1.9 (m, 1H), 2.84 (dd, 1H, J=5.1, 9.0 Hz), 3.61 (br s, 1H), 3.82 (m, 1H), 7.6-7.8 (m, 4H), 8.09 (dd, 1H, J=2.4, 6.6 Hz), 8.14 (m, 1H). 13C NMR (CDCl3): δ (ppm) 29.6, 30.7, 31.9, 40.9, 44.6, 56.8, 63.2, 112.3, 118.9, 121.5 (d, J=112.2 Hz), 129.9 (d, J=13.2 Hz), 132.7, 139.3, 140.1, 141.6, 146.5 (d, J=57.9 Hz), 157.5, 160.7.

Provenance & Evidence