Potassium Carbonate → (2R)-1-(3'-cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600915Notes

Reaction equation

HRID 1600915 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][C@@H:15]([O:32]C(=O)C2C=CC=CC=2)[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=3)=[CH:20][CH:19]=2)[CH:8]=1.C(=O)([O-])O.[Na+]>CO.O>[C:30]([C:26]1[CH:25]=[C:24]([C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:16][C@H:15]([OH:32])[CH2:14][CH2:13][C:9]3[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=3)=[CH:23][CH:22]=2)[CH:29]=[CH:28][CH:27]=1)#[N:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 53808556(2R)-4-(3-Pyridyl)-2-benzoyloxy-1-(3'-cyanobiphenyl-4-yloxy)butane

Product 1

HCID 54167436(2R)-1-(3'-cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolYield 80.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (0.21 g) was added to a solution of (2R)-4-(3-pyridyl)-2-benzoyloxy-1-(3'-cyanobiphenyl-4-yloxy)butane (0.34 g) in methanol (15 ml) and water (5 ml) and the reaction stirred for 2 hours. The mixture was then poured into saturated aqueous sodium hydrogencarbonate solution and the mixture extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as an oil (0.21 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-e9433379f86643ecba0c20e40424dd31
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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