Trifluoroacetic acid → HCID 66649710, compound

Participants

Reaction Steps

To 1,1-dimethylethyl (1S,4S)-5-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.0 g, 2.3 mmol) in DCM (10 mL) was added TFA (10 mL). After reaction was shown to be complete by TLC, the volume is reduced on the rotovap until it weighs 4 g. The solution is diluted with DCM and poured into saturated NaHCO3 solution. The layers are separated and the aqueous layer washed with DCM. The organics are combined, dried (MgSO4), filtered and rotovaped to give the title compound of step B (400 mg, 1.2 mmol, 50%). 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J=9.3 Hz, 1H), 6.37 (dd, J=9.3, 2.6 Hz, 1H), 6.27 (d, J=2.6 Hz, 1H), 3.90 (s, 3H), 3.80-3.73 (m, 2H), 3.60 (br s, 2H), 3.20 (d, J=10.6 Hz, 1H), 3.12-2.95 (m, 4H), 2.87-2.81 (m, 1H), 2.64-2.55 (m, 1H), 2.36 (d, J=9.3 Hz, 1H), 1.94-1.77 (m, 3H), 1.64 (d, J=9.3 Hz, 1H), 1.59-1.46 (m, 2H). The aqueous layer is re-extracted with EtOAc and then with 85:15 DCM:iPrOH to give more of the title compound of step B (400 mg, 1.2 mmol, 50%).

Provenance & Evidence