Water → Azetidin-3-ylbenzoate hydrochloride

HRID 1747820Notes

Reaction equation

HRID 1747820 reaction equation
[OH:1][CH:2]1[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(N(CC)CC)C.[C:20]([Cl:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C1C=CN=CC=1)C.C1COCC1>[ClH:28].[NH:4]1[CH2:3][CH:2]([O:1][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 131733564Azetidin-3-ylbenzoate hydrochlorideYield 57.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (1 g), triethylamine (1.2 mL) and DMAP (7 mg) in THF (10 ml) was added benzoylchloride (0.81 g) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, 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 dissolved in ethyl acetate (10 mL), and 4M hydrogen chloride in ethyl acetate solution (3 mL) was added. The reaction mixture was stirred at room temperature for 2 hr, and the precipitate was collected by filtration to give the title compound (710 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. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  6. addition4M hydrogen chloride in ethyl acetate solution (3 mL) was added
  7. stirringThe reaction mixture was stirred at room temperature for 2 hr
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d6478a04853e4183804d3522aaba5306
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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