Ammonium Chloride → 2-Phenylazetidine

HRID 1013103Notes

Reaction equation

HRID 1013103 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]2[NH:16][C:15](=O)[CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[NH4+]>CCOCC>[C:7]1([CH:13]2[CH2:14][CH2:15][NH:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

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

Product 1

HCID 5689712-PhenylazetidineYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add lithium aluminum hydride (685 mg, 18.1 mmol) to anhydrous ether (20 mL), followed by 4-phenyl-2-azetidinone (760 mg, 5.2 mmol). Heat the mixture to reflux for 4 hr, cool to RT. Add 20% aqueous ammonium chloride solution to quench the reaction, filter through Celite®, concentrate and purify (silica gel chromatography, eluting with 10:90 2 M ammonia in methanol:DCM) to give the title compound as a colorless oil (380 mg, 55%).

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 4 hr
  3. customto quench
  4. customthe reaction
  5. filtrationfilter through Celite®
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 10:90 2 M ammonia in methanol:DCM)

Sources & evidence

ORD record
ord-ff7f59f77e04459e806f69307ed8cfb0
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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