Potassium Carbonate → {1-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidin-3-yl}methanol

HRID 1620571Notes

Reaction equation

HRID 1620571 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]([F:16])([F:15])[F:14].Cl.[NH:18]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19]1.C(=O)([O-])[O-].[K+].[K+].O.C(OCC)(=O)C>CN(C)C=O>[F:14][C:13]([F:16])([F:15])[C:4]1[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:3]=1[CH2:2][N:18]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 22728543Water ethylacetateHCID 23080030(Pyrrolidin-3-yl)methanol hydrochloride

Product 1

HCID 86678748{1-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidin-3-yl}methanolYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (7.29 g) in N,N-dimethylformamide (10 mL) were added pyrrolidin-3-ylmethanol hydrochloride (4.9 g) and potassium carbonate (9.84 g), and the mixture was stirred at room temperature for 3 hr. Water/ethyl acetate were added to the reaction mixture, and the organic layer was separated, 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 (ethyl acetate/hexane) to give the title compound (5.00 g).

Workup

  1. customthe organic layer was separated
  2. washwashed 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 (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2a640e1372d14c3cbf9783f18e90b896
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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