Sodium Carbonate → 1-[3-Methoxy-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol

HRID 2198052

Reaction equation

HRID 2198052 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].Br[CH2:15][CH:16]([OH:20])[CH2:17][CH2:18]Br.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:6]2[CH2:18][CH2:17][CH:16]([OH:20])[CH2:15]2)[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 295701,4-Dibromo-2-butanolHCID 6056715-(Trifluoromethyl)-m-anisidine

Product 1

HCID 670222831-[3-Methoxy-5-(trifluoromethyl)phenyl]pyrrolidin-3-olYield 47%

Procedure

3-Methoxy-5-(trifluoromethyl)aniline (15.0 g) and 1,4-dibromobutan-2-ol (18.3 g) were stirred at 100° C. for 3 hr. After cooling to room temperature, to the reaction mixture was added saturated aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-50:50) to give the title compound (9.57 g, yield 47%) as an orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-50:50)

Sources & evidence

ORD record
ord-3ccd6a71f3a2457f9a639a45b543f266
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Linked notes

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