(1,1'-Biphenyl)-2-ol → HCID 54333729, compound

HRID 1682551Notes

Reaction equation

HRID 1682551 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br.[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27]Br)[CH2:21]1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(CC(C)C)=O>[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:21]1)=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 11430Potassium CarbonateHCID 70009171(R)-1-(2-bromoethyl)nipecotic acid ethyl ester hydrobromide

Product 1

HCID 54333729HCID 54333729, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Procedure

A mixture of 2-hydroxybiphenyl (3.0 g, 17.6 mmol), (R)-1-(2-bromoethyl)-3-piperidinecarboxylic acid ethyl ester hydrobromide (6.1 g, 17.6 mmol, EP 374801), potassium carbonate (9.7 g, 71 mmol) and methyl isobutylketone (50 ml) was heated at reflux for 22 h. The reaction mixture was allowed to cool, diluted with methyl isobutylketone and filtered. The solvent was evaporated in vacuo and the residue was purified by column chromatography (heptane/ethyl acetate=2/3) to give 2.7 g of (R)-1-(2-(2-phenylphenoxy) ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 h
  3. temperatureto cool
  4. filtrationfiltered
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by column chromatography (heptane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-c3abc15df1fc4a14864bc0e8c07d2f66
Source dataset
uspto-grants-1997_06
Patent number
US05635518

Reaction notes

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