Hydrochloric Acid → HCID 59404397, compound

Participants

Reaction Steps

To a solution of (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (200 mg, 450 μmol) in DCM (5 mL) under a nitrogen atmosphere was added 4M HCl in dioxane (1.7 mL, 6.8 mmol). The mixture was stirred at room temperature for 2 h. The solvent was then removed under vacuum and the residue dissolved in DCM (5 mL). DIPEA (320 μL, 1.8 mmol) and 3,3-dimethylbutanoyl chloride (72 mg, 0.54 μmol) were added and the mixture stirred at roomt for 16 h. The solvent was removed under vacuum and the residue dissolved in DCM, washed with saturated sodium carbonate solution and water and evaporated. The residue was purified by column chromatography (SiO2, EtOAc/hexanes). The resulting solid was recrystallised from methanol to yield 1-[(3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidin-1-yl]-3,3-dimethyl-butan-1-one as a white solid (106 mg, 53%). M.p.=202-204° C.; 1H NMR (400 MHz, DMSO-d6) δ: 10.82 (dd, J=7.2 and 1.6 Hz, 1H), 7.56 (dd, J=14.0 and 8.0 Hz, 1H), 7.38 (dd, J=13.6 and 8.0 Hz, 1H), 7.30-7.18 (m, 3H), 7.02 (t, J=8.0 Hz, 1H), 6.93 (m, 1H), 6.86 (m, 1H), 6.77 (m, 1H), 4.21-3.89 (m, 6H), 3.65-3.36 (m, 2H), 2.83 (t, J=5.6 Hz, 2H), 2.21 (s, 2H), 2.04 (m, 2H), 1.04 (s, 9H). LCMS: m/e 440.20 [M+H].

Provenance & Evidence