Potassium Carbonate → 4-(4-Chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 504464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504464
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](OS(C)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:10][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Produkt 1

HCID 577501934-(4-Chloro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 5-chloro-2-hydroxy-benzaldehyde (3.15 g, 20 mmol), KI (0.1 g) and K2CO3 (8.28 g, 60 mmol) in DMF (100 mL) was added 4-methanesulfonyloxy-piperidine-1-caboxylic acid tert-butyl ester (7.26 g, 26 mmol). The mixture was heated at 100° C. for 2 h, then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N NaOH (30 mL), water, and dried over anhydrous Na2SO4, concentrated to give the title compound as white solid (Yield: 5.3 g, 78%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1N NaOH (30 mL), water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-161b2d1793d5411798675f7de360f4de
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776875B2

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