Borane → 4-Benzenesulfonyl-2-(3'-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazine

Participants

Reaction Conditions

Reaction Steps

A solution of borane in THF (1M, 274.4 μL) was added to a solution of 4-benzenesulfonyl-6-(3′-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazin-2-one (50 mg) in THF (1.5 mL). The reaction mixture was heated to 85° C. for 3 hours. An aqueous solution of KH2PO4 (1M, 2 mL) was added slowly and the biphasic mixture was heated to 75° C. for 15 min, and then poured into a saturated solution of sodium bicarbonate. Ethyl acetate was added, the phases were separated, and the inorganic one was extracted with ethyl acetate (×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 4-benzenesulfonyl-2-(3′-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazine (14 mg, 29%) as a white foam, MS: 533.3 (M+H)+.

Provenance & Evidence