Benzophenone imine → HCID 68832310, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-bromophenyl)tetrahydro-2H-pyran-4-carbonitrile (1.7 g) obtained in Step A of Example 249, diphenylmethanimine (1.4 g), tris(dibenzylideneacetone)dipalladium(0) (88 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (130 mg) in toluene (50 mL) was added sodium 2-methylpropan-2-olate (921 mg), and the mixture was stirred at 90° C. for 10 hr under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, the insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. To a solution of the residue in methanol (10 mL) were added hydroxylamine hydrochloride (440 mg) and sodium acetate (530 mg). The mixture was stirred at room temperature for 30 min, and 0.1 M aqueous sodium hydroxide solution and ethyl acetate were added thereto. The solvent was evaporated under reduced pressure, the reaction mixture was poured into water, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (910 mg).

Provenance & Evidence