Trifluoroacetic acid → 2-Amino-1-[4-cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-one

Participants

Reaction Steps

To a solution containing 38 (0.28 g, 0.53 mmol) in DCM (10 mL) was added TFA (3 mL) at ambient temperature. After 90 min, the reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc and the organic solution was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 218 mg of 39 which was used without further purification. 1H NMR (CDCl3, 300 MHz), mixture of rotamers: δ9.31 (s, 0.5H), 8.24 (s, 0.5H), 7.86 (dd, J=5.4, 8.7 Hz, 0.5H), 7.54 (dd, J=5.4, 8.7 Hz, 0.5H), 7.28 (s, 1H), 7.00 (dd, J=2.4, 9.9 Hz, 0.5H), 6.96-9.6.91 (m, 1H), 6.86-6.79 (m, 0.5H), 4.98 (app t, J=8.1 Hz, 0.5H), 4.80 (app t, J=7.8 Hz, 0.5H), 4.16-4.09 (m, 0.5H), 3.94-3.81 (m, 1.5H), 3.54-3.45 (m, 1H), 3.29-3.06 (m, 2H), 2.90-2.70 (m, 2H), 2.26-2.21 (m, 0.5H), 2.12-2.05 (m, 0.5H), 1.90-1.68 (m, 4H), 1.60-1.50 (m, 4H), 1.16 (br s, 2H), 0.80 (s, 4.5H), 0.21 (s, 4.5H) ppm. Mass spectrum, m/z [427.3] (M+H)+.

Provenance & Evidence