Tetrabutylammonium Fluoride → HCID 16679615, compound

HRID 2105345Notes

Reaction equation

HRID 2105345 reaction equation
C[SiH](C)[O:3][CH:4](C(C)(C)C(C)C)[C@H:5]1[N:10]2[C:11]3[CH:12]=[CH:13][C:14]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]4)=[CH:15][C:16]=3[CH:17]=[C:9]2[C:8](=[O:28])[NH:7][CH2:6]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:3][CH2:4][C@H:5]1[N:10]2[C:11]3[CH:12]=[CH:13][C:14]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH:25]([CH3:26])[CH3:27])[CH2:21][CH2:20]4)=[CH:15][C:16]=3[CH:17]=[C:9]2[C:8](=[O:28])[NH:7][CH2:6]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 137331242HCID 137331242, compound

Product 1

HCID 16679615HCID 16679615, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 0.2 g (0.40 mmol) (S)-4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-8-(1-isopropyl-piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one in 1 ml tetrahydrofuran was cooled down to 0° C. and treated with 0.14 ml (0.126 g, 0.48 mmol) tetra-n-butylammoniumfluoride solution (1M in tetrahydrofuran). The cooling bath was removed and after 1.5 hours stirring at room temperature the solution was poured on saturated aqueous sodium bicarbonate solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant to give 60 μg (42%) of the desired compound as a colorless semi solid.

Workup

  1. customThe cooling bath was removed and after 1.5 hours
  2. additionwas poured on saturated aqueous sodium bicarbonate solution
  3. extractionwas extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant

Sources & evidence

ORD record
ord-07727a02290341ac837cd86b95b66633
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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