Sodium Hydroxide → 1-Benzhydryl-2,2-dimethylazetidin-3-one

HRID 1437246Notes

Reaction equation

HRID 1437246 reaction equation
[CH:1]([NH:14][C:15]([CH3:20])([CH3:19])[C:16](=[O:18])[CH3:17])([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.BrBr.[OH-].[Na+]>C(O)(=O)C.Cl>[CH:1]([N:14]1[CH2:17][C:16](=[O:18])[C:15]1([CH3:20])[CH3:19])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 103783013-(Benzhydrylamino)-3-methylbutan-2-one

Product 1

HCID 103555071-Benzhydryl-2,2-dimethylazetidin-3-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Into 3-(benzhydrylamino)-3-methylbutan-2-one (6.5 g) in acetic acid (20 mL), HCl gas was blown up to saturation, and bromine (1.25 mL) was added dropwise thereto, followed by stirring for 3 hours. 20% Aqueous sodium hydroxide was added to the reaction mixture, and thereby pH of the mixture was adjusted at 14 or higher, followed by partitioning by use of carbon tetrachloride. The organic layer was washed with water. The solvent was evaporated under reduced pressure, and to the residue, N,N-dimethylformamide (30 mL) and saturated aqueous sodium hydrogencarbonate (7 mL) were added, followed by stirring for 3 minutes. The reaction mixture was partitioned between water and carbon tetrachloride. The organic layer was washed twice with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified through silica gel column chromatography, to thereby give 1-benzhydryl-2,2-dimethylazetidin-3-one as a solid (754 mg, 12%).

Workup

  1. additionwas added dropwise
  2. customby partitioning by use of carbon tetrachloride
  3. washThe organic layer was washed with water
  4. customThe solvent was evaporated under reduced pressure
  5. additionto the residue, N,N-dimethylformamide (30 mL) and saturated aqueous sodium hydrogencarbonate (7 mL) were added
  6. stirringby stirring for 3 minutes
  7. customThe reaction mixture was partitioned between water and carbon tetrachloride
  8. washThe organic layer was washed twice with saturated brine
  9. dry with materialdried over magnesium sulfate anhydrate
  10. filtrationfollowed by filtration
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-0805cbdd6edb4f4187accbf56223bf74
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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