Ethyl Acetate → 1-(4-Amino-3'-chloro-biphenyl-3-yl)-ethanol

HRID 413116Notes

Reaction equation

HRID 413116 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].[BH4-].[Na+].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]([Cl:14])[CH:9]=2)=[CH:4][C:3]=1[CH:15]([OH:17])[CH3:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 159081311-(4-Amino-3'-chloro-biphenyl-3-yl)-ethanone

Product 1

HCID 120713751-(4-Amino-3'-chloro-biphenyl-3-yl)-ethanolYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone (see example 35, 0.15 g, 0.61 mmol) in anhydrous methanol was added sodium borohydride (0.07 g, 1.03 mmol) at room temperature (rt) under nitrogen. After 15 minutes, the reaction mixture was treated with ice-water. Ethyl acetate (30 mL) was then added, the organic layer was separated, and aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (10 mL) and dried over MgSO4. After removal of solvent, the residue obtained was crystallized from toluene to afford 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanol as a white solid (0.087 g, 58%): 1H-NMR (DMSO-d6) δ7.55 (t, 1H, J=1.4 Hz), 7.50 (d, 1H, J=7.8 Hz), 7.44 (d, 1H, J=2.1 Hz), 7.39 (t, 1H, J=8.2 Hz), 7.31-7.21 (m, 2H), 6.68 (d, 1H, J=8.1 Hz), 5.25 (s, 2H), 5.20 (m, 1H), 4.83 (m, 1H), 1.35 (d, 3H, J=8.8 Hz); MS (EI) m/z 247 (M+).

Workup

  1. customthe organic layer was separated
  2. extractionaqueous layer was extracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over MgSO4
  5. customAfter removal of solvent
  6. customthe residue obtained
  7. customwas crystallized from toluene

Sources & evidence

ORD record
ord-d92745c86dff4f7ca84a766a568dc8ff
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

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