Sodium Bicarbonate → (1-{1-[2,4-Bis(trifluoromethyl)phenyl]ethyl}piperidin-4-yl)methanol

HRID 1620554Notes

Reaction equation

HRID 1620554 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17][CH2:16]1)=[CH2:14].[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[CH:13]([N:15]1[CH2:16][CH2:17][CH:18]([CH2:21][OH:22])[CH2:19][CH2:20]1)[CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86678734(1-{1-[2,4-Bis(trifluoromethyl)phenyl]ethenyl}piperidin-4-yl)methanol

Product 1

HCID 86678735(1-{1-[2,4-Bis(trifluoromethyl)phenyl]ethyl}piperidin-4-yl)methanolYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1-{1-[2,4-bis(trifluoromethyl)phenyl]ethenyl}piperidin-4-yl)methanol (12.6 g) in methanol (178 mL) was added sodium borohydride (2.02 g). The reaction mixture was stirred at room temperature for 20 min, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with 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 (10.9 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 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-08494a3b9f0d4416bf3d8b0e1a6044c9
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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