Tetrabutylammonium Fluoride → HCID 11754517, compound

HRID 1391817Notes

Reaction equation

HRID 1391817 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30]([O:32]CC[Si](C)(C)C)=[O:31])=[CH:23][CH:22]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:25][CH:26]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 58629852HCID 58629852, compound

Product 1

HCID 11754517HCID 11754517, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of 2-(trimethylsilyl)ethyl 4-{4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]phenyl}butanoate (42 mg, 0.07 mmol) in THF at rt was added, drop-wise, TBAF (70 μL of a 1.0M solution in THF, 0.07 mmol) and the mixture stirred at rt for 1.5 hours. Additional TBAF (35 μL of a 1.0M solution in THF, 0.04 mmol) was then added and the mixture left to stir at rt for 17.5 hours. The mixture was then concentrated under vacuum and the residue purified by SPE (silica, 1 g Cartridge) eluting with cyclohexane:EtOAc (gradient 25:1 to 0:1), then EtOAc:MeOH (gradient 10:1 to 0:1) to give a crude product which was purified further by mass directed auto-prep HPLC to give the title compound (6.4 mg).

Workup

  1. waitthe mixture left
  2. concentrationThe mixture was then concentrated under vacuum
  3. customthe residue purified by SPE (silica, 1 g Cartridge)
  4. washeluting with cyclohexane
  5. customEtOAc (gradient 25:1 to 0:1), then EtOAc:MeOH (gradient 10:1 to 0:1) to give a crude product which
  6. customwas purified further by mass

Sources & evidence

ORD record
ord-9fb6a731cbdb430ba89873b4f3e9cd05
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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