Potassium tert-butoxide → 1-Acetyl-5-[4-(2,2-difluoroethyl)phenyl]piperidine-3-carboxylic acid

HRID 220048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220048
CC(C)([O-])C.[K+].[C:7]([N:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([F:25])[F:24])=[CH:18][CH:17]=2)[CH2:13][CH:12]([C:26]([O:28]C)=[O:27])[CH2:11]1)(=[O:9])[CH3:8]>CO>[C:7]([N:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([F:24])[F:25])=[CH:18][CH:17]=2)[CH2:13][CH:12]([C:26]([OH:28])=[O:27])[CH2:11]1)(=[O:9])[CH3:8]

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 59606565Methyl 1-acetyl-5-[4-(2,2-difluoroethyl)phenyl]piperidine-3-carboxylate

Produkt 1

HCID 596065791-Acetyl-5-[4-(2,2-difluoroethyl)phenyl]piperidine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

410 mg (3.65 mmol) of potassium tert-butoxide were added at RT to a solution of 205 mg (0.365 mmol, purity 61%) of the compound from Example 58A in methanol (6.9 ml). The mixture was stirred at 60° C. overnight. For workup, the methanol was removed under reduced pressure, the residue was admixed with water and the mixture was acidified (pH 1) with aqueous 1 N hydrochloric acid solution. The mixture was extracted with ethyl acetate, and the organic phase was dried with magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 153 mg (67% of theory, purity 50%)

Aufarbeitung

  1. customFor workup, the methanol was removed under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried with magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f02235104ddc49259f89ec76b46f8cb5
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202862B2

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