Triphenylphosphine → trans-1-Benzenesulfonyl-3-(3'-methanesulfonyl-biphenyl-3-yl)-4-phenyl-piperidine

Participants

Reaction Steps

To a solution of trans-1-benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidine (150 mg) and (3-methylsulfonylphenyl)boronic acid (109 mg) in a mixture of DMA/water (2.1 mL, 20:1) was added potassium fluoride (42.3 mg), tetrakis(triphenylphosphine)palladium(0) (50.5 mg) and triphenylphoshine (22.9 mg). The reaction mixture was irradiated with microwave at 160° C. at intervals up to 80 min. Water was added, the phases were separated, and the inorganic one was extracted with diethylether (×2). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, n-heptane/ethyl acetate 1:1) yielded trans-1-benzenesulfonyl-3-(3′-methanesulfonyl-biphenyl-3-yl)-4-phenyl-piperidine (51 mg, 26%) as a white foam, MS: 531.5 (M+H)+.

Provenance & Evidence