Benzophenone imine → 2-(Benzhydrylideneamino)-7-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-fluoren-9-one

Participants

Reaction Conditions

Reaction Steps

A mixture of the product of Example 61A (332 mg, 0.867 mmol), benzophenone imine (180 μL, 1.07 mmol; Aldrich), tris(dibenzylideneacetone)dipalladium (0) (Pd2 dba3; 32 mg, 0.035 mmol; Alfa), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP; 54 mg, 0.087 mmol; Strem) and sodium tert-butoxide (125 mg, 1.30 mmol; Aldrich) in 5 mL toluene was flushed with nitrogen and heated at 90° C. for 18 h. The reaction mixture was cooled to ambient temperature and filtered through diatomaceous earth, rinsing with EtOAc. After concentrating the solution under reduced pressure, the residue was purified by column chromatography (90 g silica gel, 1-12% gradient of NH4OH-MeOH (1:10) in CH2Cl2) to afford the title compound, which was slightly impure (489 mg, >100% yield): MS (DCI/NH3): m/z 484 (M+1)+.

Provenance & Evidence