Trifluoroacetic acid → HCID 10390365, compound

Participants

Reaction Steps

To a solution of 1.06 g (2.52 mmol) of the title compound from Example 30 in 10 mL of CH2Cl2 was added 10 mL of trifluoroacetic acid. After 2 h at ambient temperature the reaction was concentrated in vacuo. To 0.040 g (0.092 mmol) of this intermediate in 1 mL of dichloroethane was added 0.055 g (0.20 mmol) of 2,4-dichlorobenzaldehyde, followed by 0.066 g (0.31 mmol) of sodium triacetoxyborohydride. After 16 h at ambient temperature the reaction was quenched by the addition of 10 mL of saturated aqueous NaHCO3. The reaction was extracted with CH2Cl2 and the organic layer was dried (Na2SO4) and concentrated in vacuo. Purification by preparative thin layer chromatography (15% EtOAc in hexane) afforded the title compound as a white solid. 1H NMR (500 MHz, CDCl3) 8.79 (s, 1H), 7.45 (d, J=8.5 Hz, 1H), 7.38 (d, J=2.0 Hz, 1H), 7.25 (dd, J=2.0 Hz, J=8.5 Hz, 1H), 3.64 (s, 2H), 2.94 (t, J=4.5 Hz, 4H), 2.63 (t, J=4.5 Hz, 4H), 2.28 (m, 1H), 2.16 (s, 3H), 1.73 (m, 2H), 1.61 (m, 2H), 0.95 (t, J=7.5 Hz, 6H); mass spectrum (ES) m/e=479.1 (M+H).

Provenance & Evidence