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

HRID 1771812Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH:23]=[C:24]([O:26][CH3:27])[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]([O:26][CH3:27])[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-methoxy-benzamide (1.2 g, 3.3 mmol, 1.0 eq) in THF (50 mL) at 0° C. under N2 was added a solution of BH3 (1M in THF, 16.0 mL, 16.0 mmol, 5.0 eq) dropwise. The reaction mixture was heated at 60° C. overnight then cooled to room temperature and quenched with water. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 100:1 to 5:1) to give the title compound as a colorless oil (700 mg, 60%).

Workup

temperaturethen cooled to room temperature
customquenched with water
extractionThe aqueous layer was extracted with EtOAc
washthe combined organic extracts were washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue obtained
customwas purified by column chromatography (petroleum ether:EtOAc, 100:1 to 5:1)

Sources & evidence

ORD record: ord-e03f5d8dec694dfdbe6317d61748e2af
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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