Methyl 2-(phenoxymethyl)isonicotinate → Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylate

HRID 1963243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963243
[O:1]([CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=1)[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Pt](=O)=O>[CH:2]1([O:1][CH2:8][CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

4

Edukt 1

HCID 59536560Methyl 2-(phenoxymethyl)isonicotinate

Produkt 1

HCID 59536562Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylateAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Methyl 2-(phenoxymethyl)isonicotinate (2.6 g, 10.69 mmol) was dissolved in acetic acid (50 mL), then platinum(IV) oxide (0.243 g, 1.07 mmol) was added and the mixture hydrogenated in a Büchi hydrogenator at 5 bar and room temperature for 6 h. The catalyst was removed by filtration and the solvent evaporated. The residue was taken up in DCM and the organic phase was washed with satd NaHCO3. The aqueous phase was extracted with DCM and the combined organic phases were filtered through a phase separator and evaporated. Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylate (2 g, 73%) was isolated.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. washthe organic phase was washed with satd NaHCO3
  4. extractionThe aqueous phase was extracted with DCM
  5. filtrationthe combined organic phases were filtered through a phase separator
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cf814eaacbf444218c2a998d618227e1
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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