Lithium Hydroxide → 1-Phenylpiperidine-4-carboxylic acid

HRID 1178059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178059
[Li+].[OH-].C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6]>C1COCC1.CO.O>[C:13]1([N:10]2[CH2:11][CH2:12][CH:7]([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 59559569Methyl 1-phenylpiperidine-4-carboxylate

Produkt 1

HCID 30239901-Phenylpiperidine-4-carboxylic acidAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

LiOH (43 mg, 1.03 mmol) was added at room temperature to a stirred solution of 1-phenyl-piperidine-4-carboxylic acid methyl ester (150 mg, 0.68 mmol) in THF:MeOH:H2O (3:1:1, 3.2 mL). The resulting mixture was stirred at room temperature overnight. The MeOH and THF were evaporated and the residue was diluted with water (2 mL), acidified with citric acid solution and extracted with EtOAc. The organic layer was washed with saturated brine, dried over Na2SO4 and concentrated under reduced pressure to afford 94 mg (67.14% yield) of 1-phenyl-piperidine-4-carboxylic acid. LCMS purity: 95.98%.

Aufarbeitung

  1. customThe MeOH and THF were evaporated
  2. additionthe residue was diluted with water (2 mL)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-76b049cadfc14dec8fa84d59df357cba
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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