Tetrabutylammonium Fluoride → HCID 67583568, compound

HRID 1456560Notes

Reaction equation

HRID 1456560 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][C@H:9]1[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[CH:34]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67584773HCID 67584773, compound

Product 1

HCID 67583568HCID 67583568, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

580 mg of (2R,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-[2-{2-[2-(3,4-difluorophenyl)ethyl]-4-fluorophenoxy}ethyl]pyrrolidine [prepared as described in step (a) above] were dissolved in 5 ml of tetrahydrofuran, and then 0.31 ml of tetrabutylammonium fluoride were added to the resulting solution. The resulting mixture was then stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the concentrated oily substance was purified by silica gel column chromatography, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 280 mg (yield 61%) of the title compound as a colorless solid substance.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe concentrated oily substance was purified by silica gel column chromatography
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-ff0a4c8cecd445f48c03cb15fde39186
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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