Tetrabutylammonium Fluoride → HCID 54502309, compound

HRID 1456556Notes

Reaction equation

HRID 1456556 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][CH:36]=[CH:35][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][CH:36]=[CH:35][CH:34]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53877636HCID 53877636, compound

Product 1

HCID 54502309HCID 54502309, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1490 mg of (2R,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-{2-[4-fluoro-2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine [prepared as described in Example 5(a)] were dissolved in 15 ml of tetrahydrofuran, and then 0.79 ml of tetrabutylammonium fluoride were added to the resulting solution. The resulting mixture was then stirred at room temperature for 0.5 hours. At the end of this time, the reaction solution was concentrated by evaporation under reduced pressure, and the resulting 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 1115 mg (yield 95%) of the title compound as a colorless solid substance.

Workup

  1. concentrationAt the end of this time, the reaction solution was concentrated by evaporation under reduced pressure
  2. customthe resulting 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-13c7fcadd6854f88bbd467c6c2c2f658
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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