Ethyl Acetate → 1-(4-Amino-3'-fluoro[1,1'-biphenyl]-3-yl)ethanol

HRID 50734Notes

Reaction equation

HRID 50734 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].[BH4-].[Na+].S([O-])([O-])(=O)=O.[NH4+].[NH4+].C(OCC)(=O)C>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH:15]([OH:17])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 6097028Ammonium SulfateHCID 220218911-(4-Amino-3'-fluoro[1,1'-biphenyl]-3-yl)ethanone

Product 1

HCID 220218991-(4-Amino-3'-fluoro[1,1'-biphenyl]-3-yl)ethanolYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(4-amino-3′-fluoro[1,1′-biphenyl]-3-yl)ethanone (3 g, 13 mmol) in anhydrous methanol (60 mL) was treated at rt under nitrogen with sodium borohydride in a portion wise manner. After addition, the reaction mixture was stirred for 4 hours, treated with a saturated aqueous ammonium sulfate solution (50 mL) and ethyl acetate (100 mL). The organic layer was separated, dried (MgSO4) and evaporated. The residue was purified on a silica gel column chromatography (hexane:ethyl acetate/3:1) to yield 1-(4-amino-3′-fluoro[1,1′-biphenyl]-3-yl)ethanol as a white solid (2 g, 67%): mp 136-137° C.

Workup

  1. additionAfter addition
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified on a silica gel column chromatography (hexane:ethyl acetate/3:1)

Sources & evidence

ORD record
ord-f4797b5fcdf04f7aa4a77f4ea31c165e
Source dataset
uspto-grants-2004_03
Patent number
US06713478B2

Reaction notes

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