Benzoyl chloride → (3-hydroxyazetidin-1-yl)(phenyl)Methanone

HRID 2041967Notes

Reaction equation

HRID 2041967 reaction equation
Cl.[OH:2][CH:3]1[CH2:6][NH:5][CH2:4]1.[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[OH:2][CH:3]1[CH2:6][N:5]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:14])[CH2:4]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 20352194(3-hydroxyazetidin-1-yl)(phenyl)MethanoneYield 83.4%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

To a stirred mixture of 3-hydroxyazetidine hydrochloride (10.0 g, 91.3 mmol), benzoyl chloride (12.8 g, 91.3 mmol) in 3:2 water/ethyl acetate (500 mL) was added potassium carbonate (63.1 g, 456.5 mmol) at room temperature. After 16 h the organic layer was separated and concentrated under reduced pressure. The resulting residue was dissolved in 2:1 THF/methanol (150 mL) and stirred with 1.0 N sodium hydroxide (50.0 mL) at room temperature. After 1 h the reaction mixture was concentrated under reduced pressure, the resulting residue was partitioned between ethyl acetate and water and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure to provide (3-hydroxyazetidin-1-yl)(phenyl)methanone (13.5 g, 83%) as a colorless gum-like substance.

Workup

  1. customAfter 16 h the organic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 2:1 THF/methanol (150 mL)
  4. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  5. customthe resulting residue was partitioned between ethyl acetate and water
  6. customseparated
  7. washThe organic layer was washed with saturated sodium chloride
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bdbe83a0ee294e8dbd64e3cc9ae597a3
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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