Hydrochloric Acid → HCID 59199417, compound

Participants

Reaction Conditions

Reaction Steps

To a 1.25 M anhydrous methanol solution of HCl (3 mL) is added 3-(4-hydroxy-2,2,4-trimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester, which can be prepared as described in Example 38, (85 mg, 0.27 mmol). The reaction is then heated to 50° C., and is then concentrated to dryness. The resulting residue is purified by silica gel flash chromatography (diethylamine-methanol-dichloromethane, 0.5:1:98.5) to provide 3-(2,2,4-trimethyl-1,2-dihydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 297.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.86 (s, 3 H), 1.13 (s, 3 H), 2.15 (d, J=1.3 Hz, 3 H), 3.91 (s, 3 H), 5.56 (s, 1 H), 6.31 (s, 1 H), 7.16-7.26 (m, 2 H), 7.31-7.41 (m, 2 H), 7.43 (s, 1 H), 7.70 (s, 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 afford the HCl salt of 3-(2,2,4-trimethyl-1,2-dihydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester.

Provenance & Evidence