Water → 1-(Diphenylmethyl)azetidin-3-one

HRID 1622202Notes

Reaction equation

HRID 1622202 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.O.C(OCC)(=O)C>CS(C)=O>[CH:1]([N:14]1[CH2:17][C:16](=[O:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneYield 79%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

That is, to a solution of 27.27 g of 1-benzhydrylazetan-3-ol dissolved in 225 ml of dimethylsulfoxide was added 135.5 ml of triethylamine, 59.80 g of sulfur trioxide-pyridine complex was added thereto under ice-cooling, and the mixture was stirred at room temperature for 2.5 hours. To the reaction mixture were added water and ethyl acetate, the mixture was stirred and the liquids were separated. The organic layer was washed with a saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to obtain 21.35 g of 1-benzhydrylazetidin-3-one.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringthe mixture was stirred
  4. customthe liquids were separated
  5. washThe organic layer was washed with a saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-b335fd1f9085426993a160b444f0f0d9
Source dataset
uspto-grants-2014_07
Patent number
US08778628B2

Reaction notes

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