Water → 4-Fluoro-3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]-2-methyl-phenol
Reaktionsgleichung
[F:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:13]=[C:12]([CH3:23])[C:11]=2[O:24][CH3:25])=[C:6]([CH3:27])[C:5]([OH:28])=[CH:4][CH:3]=1.O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([CH3:27])[C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[CH:13]=[C:12]([CH3:23])[C:11]=1[O:24][CH3:25]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a solution of N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-5-(3-fluorophenyl)-2-methoxy-3-methyl-benzamide (450 mg, 1.17 mmol, 1.0 eq) in THF (6 mL) at 0° C. under N2 was added a solution of BH3 (1M in THF, 7.04 mL, 7.04 mmol, 6.0 eq). The reaction mixture was heated at 60° C. for 1 h. After cooling to 0° C., water was added dropwise 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, 20:1 to 10:1) to give the title compound as a colorless oil (94 mg, 22%).
Aufarbeitung
- temperatureAfter cooling to 0° C.
- 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, 20:1 to 10:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-039380dbf52e4b8fb2cc9147c11d082b
- Quelldatensatz
- uspto-grants-2016_02
- Patentnummer
- US09249085B2
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