Tetrabutylammonium Fluoride → HCID 66783250, compound

HRID 1096262Notes

Reaction equation

HRID 1096262 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][CH:9]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[CH:15]([CH3:29])[C:14]1=[O:30])[CH2:10][O:11][CH3:12])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][CH2:7][CH2:8][CH:9]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=2)[CH:15]([CH3:29])[C:14]1=[O:30])[CH2:10][O:11][CH3:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66783138HCID 66783138, compound

Product 1

HCID 66783250HCID 66783250, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethyl-propyl]-3-methyl-4-(3-trifluoromethyl-phenyl)-piperazin-2-one (139 mg, 0.23 mmol) in THF (3 mL) was added tetrabutylammonium fluoride solution (1 M in THF, 0.28 mL, 0.28 mmol) at 0° C., then after 2 h the reaction mixture was partitioned between sat. aq. NaHCO3 solution and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc/MeOH 19:1) afforded the title compound (44 mg, 52%) as a colorless oil.

Workup

  1. customafter 2 h the reaction mixture was partitioned between sat. aq. NaHCO3 solution and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-08184d8c1b04443a94c2036491671a8a
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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