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

HRID 1747819Notes

Reaction equation

HRID 1747819 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.C(=O)([O-])O.[Na+].C1COCC1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:18]1([C:17]([N:2]2[CH2:5][CH:4]([OH:6])[CH2:3]2)=[O:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 20352194(3-hydroxyazetidin-1-yl)(phenyl)MethanoneYield 78.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of azetidin-3-ol hydrochloride (200 mg), saturated aqueous sodium hydrogen carbonate solution (2 mL) and THF (2 mL) was added benzoylchloride (132 mg) under ice-cooling. The reaction mixture was stirred at room temperature for 3 days, water was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (130 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-a5d1bd322343430cb13a41200e0c7f5c
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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