Formic Acid → 2-Methyl-2-(1-methyl-piperidin-3(r,s)-yl)-propionic acid methyl ester

HRID 499709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499709
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]([CH3:13])([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[CH3:6].[CH:15](O)=O.C=O>[OH-].[Na+]>[CH3:2][O:3][C:4](=[O:14])[C:5]([CH3:6])([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH3:15])[CH2:8]1)[CH3:13]

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 66887928Methyl 2-methyl-2-(piperidin-3-yl)propanoate hydrochloride

Produkt 1

HCID 668891612-Methyl-2-(1-methyl-piperidin-3(r,s)-yl)-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

0.370 g of 2-methyl-2-piperidin-3(R,S)-yl-propionic acid methyl ester hydrochloride are dissolved in 0.5 ml of 3M NaOH. 2 ml of formic acid and 0.19 ml of formaldehyde (35% aqueous solution) are added and the reaction solution is warmed to 60° C. for 20 hours. The solution is cooled to room temperature, neutralised with 3M NaOH to pH 8-9 and extracted with dichloromethane (3×10 ml). The combined organic phases are washed with water (10 ml), dried over sodium sulphate and concentrated by evaporation. The residue is purified by means of flash chromatography (SiO2 60 F) to provide the title compound as a colourless oil. Rf 0.19 (200:20:1 dichlormethane-methanol-25% conc. ammonia).

Aufarbeitung

  1. temperatureThe solution is cooled to room temperature
  2. extractionextracted with dichloromethane (3×10 ml)
  3. washThe combined organic phases are washed with water (10 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by means of flash chromatography (SiO2 60 F)

Quellen und Nachweise

ORD-Eintrag
ord-f1fe8482986d4022bcae8b2ed1b14006
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767690B2

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