3-(3-Fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-5-methyl-benzamide → 3-[[3-(3-Fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dimethyl-phenol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:23]=[C:24]([CH3:26])[CH:25]=2)[C:11]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[CH3:22])=O)[CH:5]=[CH:6][CH:7]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:11][NH:13][C:14]3[C:15]([CH3:22])=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=3[CH3:20])[CH:23]=[C:24]([CH3:26])[CH:25]=2)[CH:5]=[CH:6][CH:7]=1Participants
3
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 3-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-5-methyl-benzamide (288 mg, 0.82 mmol, 1.0 eq) in THF (10 mL) under N2 was added a solution of BH3 (1M in THF, 5.0 mL, 5.0 mmol, 6.0 eq) at 0° C. The reaction mixture was heated at 60° C. overnight. After cooling, the resulting mixture was quenched with water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 50:1 to 20:1) to give the title compound as a colorless oil (168 mg, 61%).