Tetrabutylammonium Fluoride → 2-Hydroxyquinoline

HRID 1966653Notes

Reaction equation

HRID 1966653 reaction equation
C(O[C:9]1[CH:10]=[CH:11][C:12]([C@@H](O[Si](C(C)(C)C)(C)C)CNCCCCCCOCC(F)(F)C2C=CC=CC=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:16]1=[O:19]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 509930818-(benzyloxy)-5-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}ethyl)quinolin-2(1H)-one

Product 1

HCID 60382-HydroxyquinolineYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 72 (6.4 g, 9.63 mmol) in tetrahydrofuran (60 mL) was added tetra-n-butyl ammonium fluoride (5.02 g, 19.26 mmol). The mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. Purification by column chromatography using methylene chloride/methanol (from 95:5 to 85:15) as eluent gave 8-(benzyloxy)-5-((1R)-2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino)}-1-hydroxy ethy)quinolin-2(1H)-one (1.1 g, 20%) as oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-b9828278f3e34539bd1bb796808b930d
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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