Ammonium Chloride → 2-Phenylazetidine

HRID 528766Notes

Reaction equation

HRID 528766 reaction equation
[C:1]1([CH:7]2[NH:10][C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C1COCC1>[C:1]1([CH:7]2[CH2:8][CH2:9][NH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5688184-Phenylazetidin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 5689712-Phenylazetidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.5 g (3.4 mmol) 4-phenyl-2-azetidinone in 5 mL anhydrous THF under nitrogen was added a solution of lithium aluminium hydride (1 M in THF, 11.9 mmol) dropwise, and the mixture was heated at reflux for 4 hours. The reaction mixture was cooled to room temperature, 20% aqueous ammonium chloride was added and the mixture was filtered through a pad of celite. The filtrate was extracted with EtOAc (2×10 mL), the organic layers were combined and dried over Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, DCM/7 N ammonia in MeOH 92:2 to 94:6), which was used in the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationthe mixture was filtered through a pad of celite
  4. extractionThe filtrate was extracted with EtOAc (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and evaporation of the solvent the product
  7. customwas purified by column chromatography (silica, DCM/7 N ammonia in MeOH 92:2 to 94:6), which
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-379a35cd30244dc0b8c3b19fd11154f2
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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