Sodium hydride → 5-Benzyl-1-oxa-5-azaspiro[2.5]octane

HRID 988791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988791
[I-].[CH3:2][S+](C)C.[H-].[Na+].O.Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CS(C)=O>[CH2:10]([N:17]1[CH2:22][CH2:21][CH2:20][C:19]2([O:23][CH2:2]2)[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 27608961-Benzylpiperidin-3-one hydrochloride hydrate

Produkt 1

HCID 137207665-Benzyl-1-oxa-5-azaspiro[2.5]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel3×

Versuchsvorschrift

Trimethylsulfonium iodide (2.13 g, 10.4 mmol) in DMSO (15 mL) was added to NaH (0.4907 g, 20.4 mmol) in DMSO (70 mL). 1-benzyl-3-piperidone hydrochloride hydrate (109) (0.996 g, 4.41 mmol) was taken up in DMSO (15 mL) and was added to the reaction mixture at room temperature. When the reaction was judged complete by TLC (0.5 h), the reaction was poured over ice and the product was extracted with CH2Cl2. The organics were washed with H2O, dried over sodium sulfate, filtered and concentrated in vacuo. Purification with alumina gel chromatography (900:100:3 CH2Cl2:Hexanes:2 N NH3 in EtOH) provided pure 5-benzyl-1-oxa-5-azaspiro[2,5]octane (110). 13C NMR (CDCl3): 137.54, 128.69, 127.83, 126.67, 62.55, 59.28, 53.32, 52.96, 52.48, 30.90, 23.51 ppm.

Aufarbeitung

  1. additionwas added to the reaction mixture at room temperature
  2. customwas judged complete by TLC (0.5 h)
  3. additionthe reaction was poured over ice
  4. extractionthe product was extracted with CH2Cl2
  5. washThe organics were washed with H2O
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification with alumina gel chromatography (900:100:3 CH2Cl2:Hexanes:2 N NH3 in EtOH)

Quellen und Nachweise

ORD-Eintrag
ord-750840f14b244d63b6b210c319a179d5
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635661B2

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