2-Methylresorcinol → HCID 54121010, Verbindung

HRID 1871716

Reaktionsgleichung

Reaktionsgleichung von HRID 1871716
[CH3:1][C:2]([O-:5])([CH3:4])[CH3:3].[K+].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]=1[CH3:15].[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:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:29][C:28]([N:24]2[CH2:25][CH2:26][CH2:27][C@@H:23]2[C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])=[O:31])[C:9]=1[CH3:15])=[O:20])([CH3:4])([CH3:3])[CH3:1]

Komponenten

5

Edukt 3

HCID 118432-MethylresorcinolHCID 23665647Potassium tert-butoxideHCID 70037232Bromoacetyl-pyrrolidine-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 54121010HCID 54121010, VerbindungAusbeute 61 %

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) 2,6-dihydroxytoluene 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 335 mg (61 %) of the title compound as a colorless oil. MS m/e (%): 564 (M+NH4+, 100), 491 (27), 435 (71).

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-40e60df3fb1540ed92782182750b62b0
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103910

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