Dimethyl Sulfoxide → 1-(Diphenylmethyl)azetidin-3-one

HRID 1582392Notes

Reaction equation

HRID 1582392 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]([N:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[CH:11]([N:24]1[CH2:27][C:26](=[O:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of oxalyl chloride (21.6 g, 170 mmol) in CH2Cl2 (270 mL) was added DMSO (26.6 g, 340 mmol) at −78° C. Then to the mixture was added dropwise a solution of 1-benzhydryl-3-azetidinol (13.6 g, 56.7 mmol) in CH2Cl2 (68 mL). After the mixture was stirred for 30 min, to the mixture was added triethylamine (51.6 g, 510 mmol) at −78° C., and the resulting mixture was warmed to room temperature and stirred for 30 min before H2O (50 mL) was added. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 230-400 mesh, 300 g, Hexane/AcOEt=7/1 to 3/1) to give a product (10.0 g, 75%) as a yellow crystal.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, 230-400 mesh, 300 g, Hexane/AcOEt=7/1 to 3/1)

Sources & evidence

ORD record
ord-83ea33002d1047458bb975add1790cd1
Source dataset
uspto-grants-2004_05
Patent number
US06734306B2

Reaction notes

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