Sodium Bicarbonate → 4-Pyridinecarboxylic acid, 2,3,4,5-tetrahydro-6-methoxy-, ethyl ester

HRID 2047638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047638
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]1)=[O:5])[CH3:2].F[B-](F)(F)F.[CH3:18][O+](C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]=[C:8]([O:12][CH3:18])[CH2:7]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 18699051Ethyl 2-oxopiperidine-4-carboxylate

Produkt 1

HCID 672974184-Pyridinecarboxylic acid, 2,3,4,5-tetrahydro-6-methoxy-, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add 2-oxopiperidine-4-carboxylic acid ethyl ester (6.0 g, 35 mmol) to a solution of trimethyloxonium tetrafluoroborate (9.0 g, 59.6 mmol) in dichloromethane (78 mL) cooled to 0° C. Stir the reaction for 3 hours and pour into an ice cold solution of saturated aqueous sodium bicarbonate. Separate layers and extract the aqueous layer with additional dichloromethane. Combine the organic layers, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to afford the title compound which was used without further purification (5.87 g, 90%). Mass spectrum (m/z): 186 (M+1).

Aufarbeitung

  1. customthe reaction for 3 hours
  2. extractionSeparate layers and extract the aqueous layer with additional dichloromethane
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-16b0ec4e9c0946c99df2d2b2cdf2ec10
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592590B2

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