2-Fluoro-5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)benzamide → 3-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluoro-5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)benzamide (400 mg, 1.13 mmol, 1.0 eq) in THF under N2 was added dropwise a solution of BH3 (5.65 mL, 1M in THF, 5.65 mmol, 5.0 eq). The reaction mixture was heated to 60° C. and stirred under N2 for 3 h. After cooling, the resulting mixture was quenched by addition of 1 M HCl and water and the aqueous layer extracted with EtOAc. The organic extract was dried (Na2SO4), filtered, evaporated in vacuo and purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title product as yellow oil (340 mg, 89%).

Provenance & Evidence