Ethyl Acetate → HCID 68945104, compound

HRID 2425457Notes

Reaction equation

HRID 2425457 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].Br[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(OCC)(=O)C>O1CCCC1.O>[N:2]1([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 12308726Azetidine hydrochloride

Product 1

HCID 68945104HCID 68945104, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of azetidine hydrochloride (1 g, Aldrich) in a mixture of tetrahydrofuran (20 ml) and water (5 ml) was added with 2 N aqueous sodium hydroxide (10.7 ml) at 0° C., and then gradually added with tert-butyl bromoacetate (1.052 ml), and the mixture was stirred at the same temperature for 10 minutes, and further stirred at room temperature for 45 minutes. The reaction mixture was added with water and ethyl acetate, and the organic layer was separated. The aqueous layer was extracted three times with ethyl acetate, the combined organic layer was washed three times with saturated brine, and the solvent was evaporated under reduced pressure to obtain the title compound (688 mg).

Workup

  1. stirringfurther stirred at room temperature for 45 minutes
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washthe combined organic layer was washed three times with saturated brine
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-01a0604c49254ebdb68794628b49d0c8
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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