Potassium Carbonate → HCID 66724763, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (4R)-4-(4-chloro-3-hydroxyphenyl)-2-oxopyrrolidinecarboxylate (68a) (1.0 equiv.) in ethanol (0.4M) was added K2CO3 (2 equiv.) followed by an appropriate electrophile (1.5 equiv., e.g. 4-bromomethylpyridine hydrobromide). The reaction mixture was heated overnight at 90° C. The mixture was cooled to room temperature and the solvent removed. The crude residue was treated with a 6N HCl aqueous solution (0.1M) and heated for 3 h at 90° C. The title compound (68) was obtained following purification by HPLC purification. 1H-NMR (400 MHz, CD3OD): δ 2.60-2.66 (dd, J=16.4, 7.6 Hz, 1H), 2.74-2.78 (dd, J=16.4, 7.2 Hz, 1H), 3.17-3.24 (m, 1H), 5.28 (s, 2H), 8.53-8.54 (d, J=4.0 Hz, 1H), 7.56-7.57 (d, J=4 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.09-7.09 (d, J=2.0 Hz, 1H), 6.92-6.95 (d, J=4.0 Hz, 1H); MS (ESI) m/z 321.01 (M+H)+.

Provenance & Evidence