Benzophenone imine → 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine

Participants

Reaction Steps

A suspension of 5-bromo-2-(1,4-dioxaspiro[4.5]decan-7-en-8-yl)-3-methylpyridine (22.5 g) in Reference Example 105, benzophenone imine (13.9 g), palladium acetate (204 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (567 mg) and sodium tert-butoxide (10.5 g) in toluene (150 ml) was stirred for 6 hours under heating to reflux. After completion of the reaction, the mixture was allowed to cool, ice water was added thereto, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine (28 g) as a brown oil. MS (ESI) m/z: 411 (M+H)+.

Provenance & Evidence