Tetrabutylammonium Fluoride → HCID 22709543, compound

HRID 1061020Notes

Reaction equation

HRID 1061020 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH2:14][CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([CH2:20][OH:21])[CH2:14][CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54536298HCID 54536298, compound

Product 1

HCID 22709543HCID 22709543, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (10 ml), (2RS)-6-(N-tert-butoxycarbonylaminomethyl)-2-(tert-butyldimethylsilyloxymethyl)-1,2,3,4-tetrahydronaphthalene (1.09 g) was dissolved. To the resulting solution, tetra-butylammonium fluoride (a 1.0M tetrahydrofuran solution, 4.0 ml) was added, followed by stirring at room temperature for 2 hours. After concentration under reduced pressure, the concentrate was diluted with dichloromethane, washed with water and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1˜2:1), whereby a colorless solid (0.77 g, 98%) was obtained. A portion of the solid was recrystallized from a mixed solvent of hexane and ethyl acetate, whereby colorless crystals were obtained.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. additionthe concentrate was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1˜2:1), whereby a colorless solid (0.77 g, 98%)
  8. customwas obtained
  9. customA portion of the solid was recrystallized from a mixed solvent of hexane and ethyl acetate, whereby colorless crystals
  10. customwere obtained

Sources & evidence

ORD record
ord-2f192cc3aaea4f3e835355066e70048e
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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