Benzyl Bromide → HCID 21990155, compound

HRID 2377171Notes

Reaction equation

HRID 2377171 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([N:17]3[CH2:20][CH:19]([OH:21])[CH2:18]3)=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O.[Ag-]=O>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([N:17]3[CH2:20][CH:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:18]3)=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 219900491-(3-(2-(1-Benzothiophen-5-yl)ethoxy)propionyl)azetidin-3-ol

Product 1

HCID 21990155HCID 21990155, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

In 8 mL of N,N-dimethylformamide was dissolved 1.00 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]-1-(3-hydroxy-1-azetidinyl)-1-propanone, and 1.90 g of silver(I) oxide and 0.97 mL of benzyl bromide were added to the solution, after which the resulting mixture was stirred at room temperature for 31 hours. The insoluble materials were filtered off and water and ethyl acetate were added to the residue, after which the organic layer was separated. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; toluene:ethyl acetate=3:1 to 1:4) to obtain 1.00 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]-1-[3-(benzyloxy)-1-azetidinyl]-1-propanone as an oil.

Workup

  1. additionwere added to the solution
  2. filtrationThe insoluble materials were filtered off
  3. additionwater and ethyl acetate were added to the residue
  4. customafter which the organic layer was separated
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by a column chromatography (eluent; toluene:ethyl acetate=3:1 to 1:4)

Sources & evidence

ORD record
ord-970706b6409e420b8b6b9eaf511b0c24
Source dataset
uspto-grants-2008_12
Patent number
US07468443B2

Reaction notes

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