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

HRID 1771793Notizen

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH3:27])[C:11]([CH3:26])=[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]([CH3:27])[C:11]([CH3:26])=[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

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of 5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-2,3-dimethyl-benzamide (300 mg, 0.82 mmol, 1.0 eq) in THF (10 mL) under N2 was added a solution of BH3 (1M in THF, 4.1 mL, 4.1 mmol, 5.0 eq) dropwise at 0° C. The reaction mixture was heated at 60° C. overnight. After cooling, the reaction was quenched by addition of water and the aqueous layer extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1) to give the title compound as a colorless oil (90 mg, 32%).

Aufarbeitung

temperatureAfter cooling
customthe reaction was quenched by addition of water
extractionthe aqueous layer extracted with EtOAc
extractionThe organic extract
washwas washed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1)

Quellen und Nachweise

ORD-Eintrag: ord-705dbccfdcd14a39adbed5900742b40c
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09249085B2

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