Water → 1-benzylazetidin-2-one

HRID 261008Notes

Reaction equation

HRID 261008 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](OO)=O)[CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=CC=1.[OH2:18]>C(Cl)Cl>[CH2:8]([N:12]1[CH2:15][CH2:16][C:17]1=[O:18])[C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 111374451-benzylazetidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyl-2-azetidine carboxylic acid (2 mmol) was added slowly to excess oxalyl chloride at 0 degrees followed by gradual warming to 45 degrees (10 min.). The clear solution was then poured into cold, anhydrous ether, acidified with 10 drops of 70% perchloric acid and filtered to give N-benzyl-2-azetidinium perchlorate (95%). A suspension of this iminium salt in 10 ml of methylene chloride at 0 degrees was treated with 1 equivalent of 100% m-chloroperbenzoic acid followed by 2 equivalents of pyridine. The resulting reaction mixture was stirred for 40 min. and then poured into water. The organic layer was separated, washed with 5% NaHCO3 and dried over Na2SO4. Evaporation of the solvent under reduced pressure afforded N-benzyl-2-azetidinone as the sole product (70%).

Workup

  1. customThe resulting reaction mixture
  2. customThe organic layer was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-13efb7e97e6845b78d51ca9d713a1f54
Source dataset
uspto-grants-1979_08
Patent number
US04163743

Reaction notes

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