Sodium Carbonate → HCID 69052745, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R)-N-benzyl-N-[2-(4-bromophenyl)-ethyl]-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-chlorophenyl)ethanamine (850 mg) in 1,2-dimethoxyethane (9 ml) was added 4-[[tert-butyl(dimethyl)silyl]oxy]-phenylboronic acid (498 mg), tetrakis(triphenylphosphine)-palladium (88 mg) and aqueous solution of sodium carbonate (2M, 1.6 ml), and the mixture was stirred at 75° C. for 10 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. To a solution of the residue in tetrahydrofuran (10 ml) was added 1M tetrabutylammonium fluoride in tetrahydrofuran (3.6 ml), and the mixture was stirred at room temperature for 8 hours under nitrogen. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 4′-[2-[N-benzyl-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-1,1′-biphenyl-4-ol (540 mg).

Provenance & Evidence