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

HRID 1771797Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:28])[C:11]([O:26][CH3:27])=[C:12]([CH:25]=2)[C:13]([NH:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=2[CH3:24])=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]([CH3:28])[C:11]([O:26][CH3:27])=[C:12]([CH2:13][NH:15][C:16]3[C:17]([CH3:24])=[C:18]([OH:23])[CH:19]=[CH:20][C:21]=3[CH3:22])[CH:25]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-2-methoxy-3-methyl-benzamide (270 mg, 0.71 mmol, 1.0 eq) in THF (5 mL) at 0° C. under N2 was added a solution of BH3 (1M in THF, 1.07 mL, 1.07 mmol, 1.5 eq) dropwise. The reaction mixture was heated at 60° C. for 4 h, then cooled 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 30:1 to 20:1) to give the title compound as a yellow oil (115 mg, 44%)

Workup

temperaturecooled
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 30:1 to 20:1)

Sources & evidence

ORD record: ord-af5f98234cb2437c994e195485b7a03e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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