HCID 66751577, compound → HCID 59728037, compound

Participants

Reaction Conditions

Reaction Steps

Isopropyl-(3-nitro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-ylmethyl]-amine (0.2 g, 0.51 mmol) was dissolved in ethanol, palladium on charcoal (20 mg, 10% Pd) was added and the mixture was hydrogenated overnight. The catalyst was filtered off and the solvent was evaporated. The residue was dissolved in ethyl acetate and filtered over silica gel. After evaporation the residue was dissolved in hydrochloric acid in ethanol (5M, 1 ml) and stirred at 60° C. for 2 hours. The solvent was evaporated and the residue was partitioned between sodium hydroxide solution (10%) and dichloromethane. After separation the aqueous layer was extracted again with dichloromethane. The combined organic layers were dried over magnesium sulphate and evaporated. The residue was purified using flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=90:10) to yield a light yellow gum, (0.054 g, 51%); MS (ISP): 231.4 ((M+H)+.).

Provenance & Evidence