5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → 5-(4-{4-[2-(3-Chloro-phenyl)-(2R)-2-hydroxyethylamino}-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

Participants

Reaction Steps

The title compound was prepared from 5-[4-(4-oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 38) and (1R)-2-amino-1-(3-chloro-phenyl)-ethanol (which was obtained in Example 1) according to the procedure of Example 73 as a pale yellowish solid; mp>195–198° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.40–1.60 (m, 2 H), 1.85–2.10 (m, 2 H), 2.60–3.50 (m, 7 H), 3.65 (brd, J=12.5 Hz, 2 H), 4.63 (dd, J=9.5, 4.1 Hz, 1 H), 4.74 (dd, J=8.8, 3.1 Hz, 1 H), 6.86 (d, J=8.7 Hz, 2 H), 7.05 (d, J=8.7 Hz, 2 H), 7.20–7.50 (m, 4 H); MS (ES) m/z: 460.0 (MH+); HRMS Calcd. for C23H26ClN3O3S (M+): 459.1383. Found: 459.1376.

Provenance & Evidence