Tetrabutylammonium Fluoride → HCID 22709543, compound

HRID 352841Notes

Reaction equation

HRID 352841 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. Tetrabutylammonium fluoride (a 1.0 M tetrahydrofuran solution, 4.0 ml) was added to the resulting solution, followed by stirring at room temperature for 2 hours. After concentration under reduced pressure, the reaction mixture was diluted with dichloromethane, washed with water an 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 to 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 reaction mixture was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialan dried 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 to 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-8f7100baf73c44819d7e46c9b7081560
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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