Ethyl 2-(1-(2-Amino-4-hydroxyphenyl)-2-oxopyrrolidin-3-yl)acetate → Ethyl 2-(6-Hydroxy-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(1-(2-amino-4-hydroxyphenyl)-2-oxopyrrolidin-3-yl)acetate (0.740 g, 2.66 mmol) was dissolved in AcOH (50 mL) and was warmed to 75° C. and stirred for 8 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in toluene and concentrated again. The black concentrate was filtered through a plug of silica eluting with 10% MeOH in DCM. The filtrate was concentrated to provide the title compound (666 mg). LCMS m/z=261.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.19 (t, J=7.1 Hz, 3H), 2.25-2.36 (m, 1H), 2.63 (dd, J=16.4, 8.8 Hz, 1H), 2.79-2.89 (m, 2H), 3.48-3.56 (m, 1H), 3.90-3.98 (m, 1H), 4.02-4.14 (m, 2H), 6.61 (dd, J=8.6, 2.3 Hz, 1H), 6.73 (d, J=2.0 Hz, 1H), 7.30 (d, J=8.6 Hz, 1H), 9.11 (bs, 1H).

Provenance & Evidence