Tetrabutylammonium Fluoride → HCID 72574147, compound

HRID 271386Notes

Reaction equation

HRID 271386 reaction equation
[Si]([O:8][CH:9]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][CH:13]1[F:26])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:26][CH:13]1[CH:12]([O:11][CH2:10][CH:9]([OH:8])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:14]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69275819HCID 69275819, compound

Product 1

HCID 72574147HCID 72574147, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethoxy)-3-fluorocyclohexylcarbamate (5.83 g, 12.5 mmol) in THF (100 mL) was added tetrabutylammonium fluoride (25 mL, 25 mmol, 1M in THF) and the reaction mixture was stirred at room temperature for 8 h. The mixture was extracted with ethyl acetate (4×), and the combined organics washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (hexane: ethyl acetate 80:20 then 60:40) gave tert-Butyl 3-fluoro-4-(2-hydroxy-2-phenylethoxy)cyclohexylcarbamate (4.33 g) as a white solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (4×)
  2. washthe combined organics washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (hexane: ethyl acetate 80:20

Sources & evidence

ORD record
ord-96dde784a7164b38b7b985438f4de79a
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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