Cesium carbonate → 3-Neopentyl-7-(((2-nitro-5-(trifluoromethyl)phenyl)amino)methyl)-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 1423844

Reaktionsgleichung

Reaktionsgleichung von HRID 1423844
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].Br[CH2:16][CH:17]1[CH2:32][CH2:31][CH2:30][C:19]2([O:23][C:22](=[O:24])[N:21]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20]2)[CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C=O)C>[CH2:25]([N:21]1[CH2:20][C:19]2([CH2:30][CH2:31][CH2:32][CH:17]([CH2:16][NH:6][C:5]3[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:18]2)[O:23][C:22]1=[O:24])[C:26]([CH3:29])([CH3:28])[CH3:27]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 2231003-Amino-4-nitrobenzotrifluorideHCID 867187937-(Bromomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one

Produkt 1

HCID 711161003-Neopentyl-7-(((2-nitro-5-(trifluoromethyl)phenyl)amino)methyl)-1-oxa-3-azaspiro[4.5]decan-2-oneAusbeute 18,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution containing 2-nitro-5-(trifluoromethyl)aniline (0.777 g, 3.77 mmol) and 7-(bromomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (1.00 g, 3.14 mmol) in DMF (15 mL) was treated with cesium carbonate (3.07 g, 9.43 mmol) and stirred at 60° C. overnight. The cooled reaction mixture was diluted with saturated, aqueous ammonium chloride solution, and the product was extracted into DCM. The organics were washed with brine, dried over Na2SO4, and concentrated. The residue was purified on a 120 g silica gel column (10-60 EtOAc/hexanes; 65 mL/min elution; 254 nm detection) to afford the title compound (0.260 g, 19 yield). MS (m/z) 444.2 (M+H+).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionthe product was extracted into DCM
  3. washThe organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified on a 120 g silica gel column (10-60 EtOAc/hexanes; 65 mL/min elution; 254 nm detection)

Quellen und Nachweise

ORD-Eintrag
ord-b430131e6fab47568898c5403af08fa0
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927585B2

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