Water → 3-Phenylcyclobutan-1-amine

HRID 1048159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048159
[C:1]1([CH:7]2[CH2:10][C:9](=[N:11]O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:1]1([CH:7]2[CH2:8][CH:9]([NH2:11])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57357177N-(3-phenylcyclobutylidene)hydroxylamine

Produkt 1

HCID 5229613-Phenylcyclobutan-1-amineAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-phenylcyclobutanone oxime (0.167 g, 1.04 mmol) in THF (5 ml) was added 1M lithium aluminum hydride in THF (2.18 ml, 2.18 mmol) dropwise over 3 minutes. The reaction was heated to reflux for 4 hours, then cooled to ambient temperature. Water (0.083 ml), 1M sodium hydroxide (0.083 ml), and additional water (0.248 ml) were added, and the reaction was stirred an additional 30 minutes. The reaction was filtered, and the solids were washed with THF. The filtrates were combined and concentrated to yield 101 mg of the title compound (66.2% yield).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. filtrationThe reaction was filtered
  4. washthe solids were washed with THF
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-53470d92e12d4556812b6551d170c3d8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569522B2

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