1-(3,3-dimethyl-indan-1-yl)-5-vinyl-1H-imidazole → 1-(3,3-dimethyl-indan-1-yl)-5-ethyl-1H-imidazole

Participants

Reaction Steps

To a solution of 1-(3,3-dimethyl-indan-1-yl)-5-vinyl-1H-imidazole (210 mg, 0.882 mmol), which can be prepared as described in Example 27, in methanol (10 mL) under a nitrogen atmosphere is added 5 wt % palladium on carbon (˜200 mg, ˜0.09 mmol). The atmosphere of the reaction vessel is evacuated of and backfilled with hydrogen gas (balloon pressure). The reaction is permitted to stir under a hydrogen atmosphere for 2 hours and is then diluted with ethyl acetate and filtered through a pad of Celite®. The reaction mixture is concentrated and the residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:19 to 1:4) to provide 1-(3,3-dimethyl-indan-1-yl)-5-ethyl-1H-imidazole; HRMS: (ESI) m/z 241.1716 [(M+H)+; calcd for C16H21N2: 241.1705]; 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (s, 3 H), 1.31 (t, J=7.6 Hz, 3 H), 1.42 (s, 3 H), 2.04 (dd, J=12.9, 8.3 Hz, 1 H), 2.51-2.68 (m, 3 H), 5.59 (t, J=8.0 Hz, 1 H), 6.85 (d, J=1.0 Hz, 1 H), 7.04 (d, J=6.8 Hz, 1 H), 7.21-7.29 (m, 3 H), 7.33-7.38 (m, 1 H); The HCl salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCl in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCl salt of 1-(3,3-dimethyl-indan-1-yl)-5-ethyl-1H-imidazole.

Provenance & Evidence