Cyclohexane → HCID 59599682, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbaldehyde (202 mg) at room temperature in methanol (10 ml) under an argon atmosphere were added zinc chloride (409 mg) and 1,2,3,4-tetrahydroquinoline (100 mg). The clear light yellow solution was stirred for 4 hours and 30 minutes. Then, NaBH3CN (141 mg) was added in one portion. The mixture was heated to 60° C. and stirring at that temperature was continued for 22 hours. The reaction was directly adsorbed on silica gel. The crude product was isolated by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/ethyl acetate 65:35) to give 1-[5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-ylmethyl]-1,2,3,4-tetrahydroquinoline (238 mg) as colorless viscous oil. MS (ISP): 362.3 ([M+H]+).

Provenance & Evidence