Water → Methyl 1-[2,4-bis(trifluoromethyl)benzyl]azetidine-3-carboxylate

HRID 1620482Notes

Reaction equation

HRID 1620482 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][NH:7][CH2:6]1)=[O:4].Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[C:21]([F:24])([F:23])[F:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:22][C:21]([F:23])([F:24])[C:12]1[CH:13]=[C:14]([C:17]([F:20])([F:18])[F:19])[CH:15]=[CH:16][C:11]=1[CH2:10][N:7]1[CH2:8][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 20132751Methyl azetidine-3-carboxylate

Product 1

HCID 86678674Methyl 1-[2,4-bis(trifluoromethyl)benzyl]azetidine-3-carboxylateYield 36.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methylazetidine-3-carboxylate (5 g) and 1-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (13.3 g) in DMF (100 mL) was added potassium carbonate (7.20 g) at room temperature. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (5.45 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-629220928d4247478e0e9eb2bc8be9ae
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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