Dimethylformamide → Benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1518458

Reaktionsgleichung

Reaktionsgleichung von HRID 1518458
CS([O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1)(=O)=O.O[C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[O:29]=[C:25]1[CH:24]=[C:23]([O:5][CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:8][CH2:7]2)[CH:28]=[CH:27][NH:26]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 546960044-Hydroxy-2(1H)-pyridinoneHCID 58303455Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylate

Produkt 1

HCID 67366192Benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylateAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A stirring suspension of benzyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (1.97 g, 6.30 mmol), 4-hydroxypyridin-2(1H)-one (0.50 g, 4 5 mmol, Aldrich), potassium carbonate (1.43 g, 10 6 mmol, EMD) and DMF (25 mL) was heated at 140° C. for 2.5 h and then cooled to room temperature. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The organic layers were combined and washed with brine, dried over Na2SO4 and concentrated in vacuo to a light yellow oil. The oil was purified by flash chromatography (SiO2, 0 to 10% MeOH in CH2Cl2) to yield 550 mg of desired product as a white solid. MS (ESI) 329 (M+H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo to a light yellow oil
  6. customThe oil was purified by flash chromatography (SiO2, 0 to 10% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-0ef79fcebd5d4c67af83ad4952c62a89
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232404B2

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