1-Butanol → HCID 23093706, compound

Participants

Reaction Conditions

Reaction Steps

Under carbon monoxide atmosphere, 120 μl of butanol and 265 μl of tributylamine were added to a mixture of 409 mg of tert-butyl 4-[(E)-2-(4-bromo-2,6-dimethylphenyl)vinyl]piperidine-1-carboxylate and 39 mg of dichlorobistriphenylphosphine palladium. The mixture was heated at 100° C. overnight with stirring. Then 87 mg of dichlorobistriphenylphosphine palladium, 120 μl of butanol and 265 μl of tributylamine were added to the reaction mixture and the mixture was heated at 120° C. overnight with stirring. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed sequentially with 0.1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 217 mg of tert-butyl 4-{(E)-2-[4-(butoxycarbonyl)-2,6-dimethylphenyl]vinyl}piperidine-1-carboxylate (Example 32-1) and 123 mg of tert-butyl 4-((E)-2-{4-[(dibutylamino)carbonyl]-2,6-dimethylphenyl}vinyl)piperidine-1-carboxylate (Example 32-2).

Provenance & Evidence