3-Methylcatechol → HCID 54553842, Verbindung

HRID 1871727

Reaktionsgleichung

Reaktionsgleichung von HRID 1871727
[CH3:1][C:2]([O-:5])([CH3:4])[CH3:3].[K+].[CH3:7][C:8]1[CH:14]=[CH:13][CH:12]=[C:10]([OH:11])[C:9]=1[OH:15].[C:16]([O:20][C:21]([CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28](=[O:31])[CH2:29]Br)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[C:2]([O:5][C:21]([C@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28](=[O:31])[CH2:29][O:11][C:10]1[CH:12]=[CH:13][CH:14]=[C:8]([CH3:7])[C:9]=1[O:15][CH2:29][C:28]([N:24]1[CH2:25][CH2:26][CH2:27][C@@H:23]1[C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])=[O:31])=[O:20])([CH3:4])([CH3:3])[CH3:1]

Komponenten

5

Edukt 3

HCID 3403-MethylcatecholHCID 23665647Potassium tert-butoxideHCID 70037232Bromoacetyl-pyrrolidine-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 54553842HCID 54553842, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a solution of 236 mg (2.1 mmol) potassium tert-butylate in 2 ml dimethylformamide at room temperature was added dropwise a solution of 124 mg (1.0 mmol) 3-methylcatechol in 2 ml dimethylformamide. Stirring was continued for 2-3 min and a solution of 584 mg (2.0 mmol) (R)-(1) -bromoacetyl-pyrrolidine-2-carboxylic acid tert-butyl ester in 4 ml dimethylformamide was added within 1-2 min. The reaction mixture was stirred for additional 3 h at room temperature. The solvent was removed in vacuo and the residue purified by flash-chromatography to yield 356 mg (65%) of the title compound as a colorless oil. MS m/e (%): 547 (M+H+, 100), 491 (14), 435 (17).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for additional 3 h at room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by flash-chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1b3cbeac81264d908d07ddb7448c666e
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103910

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