4-Phenylazetidin-2-one → 2-Phenylazetidine

HRID 737003Notes

Reaction equation

HRID 737003 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-]>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

4

Reactant 2

HCID 5688184-Phenylazetidin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 5689712-Phenylazetidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-phenyl-azetidin-2-one (1.0 g, 4.28 mmol) in anhydrous THF (20 mL) and treat with 1.0 M solution of lithium aluminum hydride (8.57 mL, 2.0 equiv.) at room temperature. Stir for 15 h, cool to 0° C. in an ice bath and quench with 8.5 mL 1.0 M NaOH then 8.5 mL H2O. Filter resulting solution through celite with additional EtOAc, dry with MgSO4, filter and evaporate to yield a milky white oil that solidifies upon standing. Use 2-Phenyl-azetidine without further purification.

Workup

  1. customquench with 8.5 mL 1.0 M NaOH
  2. filtrationFilter
  3. customresulting solution through celite with additional EtOAc
  4. dry with materialdry with MgSO4
  5. filtrationfilter
  6. customevaporate
  7. customto yield a milky white oil
  8. customUse 2-Phenyl-azetidine without further purification

Sources & evidence

ORD record
ord-2e1cc54868fb4c7e9658e4a58c2f0033
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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