Benzophenone imine → HCID 86692519, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]-N-methylcarbamic acid-tert-butyl ester (1.25 g) in toluene (17 ml) were added palladium acetate (18 mg), benzophenone imine (0.6 ml), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (51 mg) and sodium tert-butoxide (473 mg) at room temperature, and stirred at 120° C. for 0.5 hours. Then, after the mixture was cooled to room temperature, hydroxyamine monohydrochloride (683 mg) and sodium acetate (1.6 g) were added thereto, and stirred at the same temperature for 4 hours. After completion of the reaction, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and extracted with 10% methanol/chloroform solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with basic silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (987 mg) as a pale yellow solid.

Provenance & Evidence