Triethylamine → 1-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidine-3-carbaldehyde

HRID 1620572Notes

Reaction equation

HRID 1620572 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7]1.C(N(CC)CC)C.O.C(OCC)(=O)C>CS(C)=O>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]1[CH2:10][CH2:9][CH:8]([CH:11]=[O:12])[CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22728543Water ethylacetateHCID 86678748{1-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidin-3-yl}methanol

Product 1

HCID 866787491-[2,4-Bis(trifluoromethyl)benzyl]pyrrolidine-3-carbaldehydeYield 75.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of {1-[2,4-bis(trifluoromethyl)benzyl]pyrrolidin-3-yl}methanol (4.69 g) and triethylamine (5.99 mL) in dimethyl sulfoxide (50 mL) was added sulfur trioxide pyridine complex (6.84 g), and the mixture was stirred at room temperature for 4 hr. Water/ethyl acetate were added to the reaction mixture, and the organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution 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 (3.50 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution 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-aa9e3cb6e2f44551b29688e50a07caaa
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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