Tetrabutylammonium Fluoride → HCID 54365189, compound

HRID 1600992Notes

Reaction equation

HRID 1600992 reaction equation
[Si]([O:8][C@H:9]([CH2:28][CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][C:13]=1[C:24]([F:27])([F:26])[F:25])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[N:32]1[CH:33]=[CH:34][CH:35]=[C:30]([CH2:29][CH2:28][C@@H:9]([OH:8])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][C:13]=2[C:24]([F:26])([F:27])[F:25])[CH:31]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54085371HCID 54085371, compound

Product 1

HCID 54365189HCID 54365189, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(2R)-2-(tert-Butyldimethylsilyloxy)-4-(3-pyridyl)-1-(3-trifluoromethylbiphenyl-4-yloxy)butane (0.8 g, ~67% pure) was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride (0.84 g) was added. The reaction was stirred at ambient temperature for 1 hour and was then poured into brine and extracted with ether. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure. The residue obtained was purified by reverse phase HPLC to give the title compound as a white solid (0.13 g).

Workup

  1. extractionextracted with ether
  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 reverse phase HPLC

Sources & evidence

ORD record
ord-55fb9fd4608d4c01b331a7f667bdd5c5
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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