Water → 3-Phenylcyclobutan-1-amine

HRID 1021530Notes

Reaction equation

HRID 1021530 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 5229613-Phenylcyclobutan-1-amineYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c38d9754f2e54108a9048cc9a2c5c287
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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