Trifluoroacetic acid → HCID 10363477, compound

Participants

Reaction Steps

To 50 mg (0.11 mmol) of chloroformate 6-1 in THF was added 45 μL (0.32 mmol) of triethylamine, and 32 μL (0.32 mmol) of piperidine. After stirring overnight at room temperature, ˜300 μL of trifluoroacetic acid was added and stirring was continued for 2 h. The mixture was partitioned between EtOAc and 10% KHSO4, the layers were separated, the organic phase was washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 6-2 as a white solid. Data for 6-2: 1HNMR (500 MHz, d6-DMSO) δ 7.4-7.2 (m, 8H), 6.4 (s, 1H), 5.1 (m, 1H), 4.8 (m, 1H), 4.7 (m, 1H), 4.35 (m, 1H), 4.1 (m, 1H), 3.2-3.0 (m, 4H), 1.8-1.6 (m, 6H) ppm. HRMS (ES) calc'd M+H for C23H24F2N2O2: 399.1879. Found: 399.1860.

Provenance & Evidence