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

HRID 1692324Notes

Reaction equation

HRID 1692324 reaction equation
Cl.[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]2[CH2:12][CH:11]([OH:13])[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(=O)(=O)=O.O>O1CCCC1.CS(C)=O>[C:14]1([CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]2[CH2:12][C:11](=[O:13])[CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 28017261-benzhydrylazetidin-3-ol Hydrochloride

Product 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(diphenylmethyl)azetidin-3-ol hydrochloride salt, (20 g, 72.5 mmol) in tetrahydrofuran (69 ml) and DMSO (173 ml) was added triethylamine (50.5 ml, 362.6 mmol) at 0° C. Then sulphur trioxide:pyridine complex (69 g, 433 mmol) was added portionwise to the reaction mixture over 10 minutes. The resulting yellow solution was stirred at room temperature for 2 hours. Then the reaction mixture was poured in to cold water (173 ml) and extracted with (1:1) ethyl acetate:hexane (5×200 ml). The combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml), dried over anhydrous sodium sulphate and concentrated in vacuo. Crude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane to get 11.4 g (67%) of the title compound as a white solid.

Workup

  1. extractionextracted with (1:1) ethyl acetate
  2. washThe combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customCrude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane

Sources & evidence

ORD record
ord-16fa7bc0f88f45a580be5c9717430f17
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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