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

HRID 1771789Notes

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]=1

Participants

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%).

Workup

temperatureAfter cooling
customthe resulting mixture was quenched with water
extractionextracted with EtOAc
washThe combined organic extracts were washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography (petroleum ether: EtOAc, 50:1 to 20:1)

Sources & evidence

ORD record: ord-d1d69e3aa774490c90cb69fb7d171df2
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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