Water → 4-[2-(3-Methoxypropoxy)phenyl]-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

HRID 1694906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694906
[CH3:1][O:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[Cs+].[Cs+].[C:13]([O:17][C:18]([N:20]1[CH2:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])[CH2:22][C:21]1([CH3:35])[CH3:34])=[O:19])([CH3:16])([CH3:15])[CH3:14].O>CN(C)C=O>[C:13]([O:17][C:18]([N:20]1[CH2:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:22][C:21]1([CH3:35])[CH3:34])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5245511-Bromo-3-methoxypropaneHCID 666456104-(2-Hydroxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 666455094-[2-(3-Methoxypropoxy)phenyl]-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl esterAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

450 mg of 3-methoxypropyl bromide (2.94 mmol) and 958 mg of cesium carbonate (2.94 mmol) were added to a solution of 573 mg of 4-(2-hydroxyphenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in Example (10d) (1.96 mmol) in N,N-dimethylformamide (20 ml), and the mixture was stirred at 100° C. for four hours. The reaction mixture was cooled and then water was added, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=1/1) to obtain 540 mg of the title compound (yield: 70%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-ffe28787a7ca443ab4c23513159bd168
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158790B2

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