1-(3-Cyclopentyl-propyl)-3-(4-nitro-phenyl)-1,3-dihydro-imidazol-2-one → 1-(4-Amino-phenyl)-3-(3-cyclopentyl-propyl)-imidazolidin-2-one

Participants

Reaction Steps

A mixture of the product from Example 49 (3.7 g, 11.7 mmol) and 10% palladium on activated carbon (0.74 g) in ethyl acetate (200 mL) was placed under an atmosphere of hydrogen overnight. The mixture was filtered through a pad of Celite with excess ethyl acetate, and the filtrate was concentrated to a crude brown oil. The crude was purified by silica gel chromatography (gradient elution from 2:1 hexanes/ethyl acetate to 1:1 hexanes/ethyl acetate) to afford a pale orange solid (2.01 g, 60%). Mp 97-99° C.; Rf =0.1 (2:1 hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 7.20 (d, 2 H), 6.72 (d, 1 H), 6.63 (d, 1 H), 6.57 (d, 2 H), 5.09 (br s, 1 H), 3.50 (t, 2 H), 1.72 (m, 3 H), 1.59 (m, 6 H), 1.26 (m, 2 H), 1.03 (m, 2 H); MS (FAB) m/z 286 (MH+).

Provenance & Evidence