Methyl iodide → 1,3,3-trimethyl-4-phenylazetidin-2-one

HRID 361761Notes

Reaction equation

HRID 361761 reaction equation
[H-].[Na+].[C:3]1([CH:9]2[NH:12][C:11](=[O:13])[C:10]2([CH3:15])[CH3:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:16]I.[Cl-].[NH4+]>O1CCCC1>[CH3:16][N:12]1[CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:10]([CH3:15])([CH3:14])[C:11]1=[O:13]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27542183,3-dimethyl-4-phenylazetidin-2-one

Product 1

HCID 5833921,3,3-trimethyl-4-phenylazetidin-2-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% oil) (0.48 g, 12 mmol) was added at 0° C. to a tetrahydrofuran (40 ml) solution of 4-phenyl-3,3-dimethyl-2-azetidinone (1.75 g, 10 mmol) as prepared in Example 2-(2) and the mixture was reacted at 0° C. for 15 minutes. To the reaction solution, methyl iodide (0.74 ml, 12 mol) was added dropwise and the temperature of the mixture was returned to room temperature. The reaction was performed for 2 hours and stopped by adding a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted 2 times with ethyl acetate and washed 3 times with a saturated aqueous solution of NaCl. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. The obtained oil was applied to a silica gel column and eluted with a mixed solution (hexane:ethyl acetate=2:1). The desired fractions were collected and the solvents were distilled off to yield N-methyl-4-phenyl-3,3-dimethyl-2-azetidinone (1.89 g, quant.).

Workup

  1. customthe mixture was reacted at 0° C. for 15 minutes
  2. customwas returned to room temperature
  3. extractionThe reaction mixture was extracted 2 times with ethyl acetate
  4. washwashed 3 times with a saturated aqueous solution of NaCl
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. washeluted with a mixed solution (hexane:ethyl acetate=2:1)
  8. customThe desired fractions were collected
  9. distillationthe solvents were distilled off

Sources & evidence

ORD record
ord-36902818573346f3a452e7cfbe0a3c4b
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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