Sodium borohydride → HCID 57951159, compound

HRID 1919809Notes

Reaction equation

HRID 1919809 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:25])[CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:25])[CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:23])([F:24])[F:22])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57951114HCID 57951114, compound

Product 1

HCID 57951159HCID 57951159, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stir 4-(3-fluoro-phenyl)-N-(4-trifluoromethoxy-phenyl)-4-oxo-butyramide (3.0 g, 8.5 mmol) in ethanol (70 mL) at room temperature. Add sodium borohydride (650 mg, 17.2 mmol) portionwise and stir at room temperature until TLC indicates that no starting material remains. Add acetone to quench excess borohydride, concentrate the reaction mixture under reduced pressure, redissolve in ethyl acetate and wash with brine. Dry over anhydrous magnesium sulfate, evaporate under reduced pressure to give the titled compound (2.0 g, 67% yield) MS (m/z): 358(M+1).

Workup

  1. customAdd acetone to quench excess borohydride
  2. concentrationconcentrate the reaction mixture under reduced pressure
  3. dissolutionredissolve in ethyl acetate
  4. washwash with brine
  5. dry with materialDry over anhydrous magnesium sulfate
  6. customevaporate under reduced pressure

Sources & evidence

ORD record
ord-4e2af5c27e4042378e0bcf888c2fab39
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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