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

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-5-(3-fluorophenyl)-2,3-dimethyl-benzamide (290 mg, 0.78 mmol, 1.0 eq) in THF (10 mL) was added a solution of BH3 (1M in THF, 5 mL, 5.0 mmol, 6.4 eq) under nitrogen. The mixture was heated at 60° C. overnight then the reaction quenched by addition of methanol. The mixture was evaporated in vacuo and the residue obtained purified by column chromatography (petroleum ether:EtOAc, 400:1 to 20:1) to give the title compound as a pale red oil (230 mg, 85%).

Provenance & Evidence