Ethyl Acetate → 5-Amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate

HRID 471986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471986
[C:1](=[O:22])([O:20][CH3:21])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([F:12])=[CH:5][C:4]=1[C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])=O.[NH4+].C(OCC)(=O)C>CO.[Pd]>[C:1](=[O:22])([O:20][CH3:21])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([F:12])=[CH:5][C:4]=1[C:13]1([CH3:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 593950134-Fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate

Produkt 1

HCID 513584455-Amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonateAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate 24.1 g, 77.5 mmol) in 220 mL of CH3OH was added Pd/C 10%, 9.6 g, then ammonium formate (26.7 g, 445 mmol) was portion-wise added to the above reaction mixture at room temperature until starting material is consumed. The mixture was filtrated and the filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel diluted with hexane:ethyl acetate=50:1 to give 5-amino-4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate as a red brown oil (17.9 g, 82% yield). 1H NMR (400 MHz, CDCl3) δ 6.99 (d, J=13.6 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 3.89 (s, 3H), 3.43 (brs, 2H), 1.96-1.91 (m, 2H), 1.58-1.38 (m, 8H), 1.18 (s, 3H): MS m/z: 281.9 [M+H]

Aufarbeitung

  1. additionadded to the above reaction mixture at room temperature
  2. customis consumed
  3. filtrationThe mixture was filtrated
  4. customthe filtrate was evaporated under vacuum
  5. customThe residue was purified by column chromatography on silica gel
  6. additiondiluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-4ee6b286ce0046298c47b6fae48d6e40
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633189B2

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