Phosphoric Acid → 1-(Diphenylmethyl)azetidin-3-one

HRID 622676Notes

Reaction equation

HRID 622676 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.N1C=CC=CC=1.P(=O)(O)(O)O.C1(N=C=NC2CCCCC2)CCCCC1>CS(C)=O.C(Cl)Cl.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

8

Reactant 4

HCID 1004Phosphoric AcidHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneYield 68%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

7.17 g (0.03 mole) of 1-benzhydryl-3-hydroxyazetidine were dissolved in a mixture of 35 ml of dimethyl sulfoxide and 20 ml of methylene chloride. 1 ml of pyridine, 0.5 ml of phosphoric acid and then 12.5 g (0.06 mole) of 1,3-dicyclohexylcarbodiimide were added, in turn, to the resulting solution. The reaction mixture was then stirred for 2 hours, after which water was added to it. The reaction mixture was then extracted twice, each time with 200 ml of chloroform. The combined extracts were dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The concentrate was subjected to silica gel column chromatography, and 4.84 g (67%) of 1-benzhydryl-3-oxoazetidine were obtained from the fractions eluted with a 9:1 by volume mixture of toluene and ethyl acetate.

Workup

  1. extractionThe reaction mixture was then extracted twice
  2. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  3. distillationthe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-56b8f97e015049bb868b07d6167c8b44
Source dataset
uspto-grants-1988_09
Patent number
US04772596

Reaction notes

Loading…