Tetrabutylammonium Fluoride → HCID 25205716, compound

HRID 660191Notes

Reaction equation

HRID 660191 reaction equation
[CH2:1]([S:6][C:7]1[N:11]=[CH:10][N:9](COCC[Si](C)(C)C)[C:8]=1[C:20]1[CH2:21][N:22]([CH3:26])[CH2:23][CH2:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH3:5].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([S:6][C:7]1[N:11]=[CH:10][NH:9][C:8]=1[C:20]1[CH2:21][N:22]([CH3:26])[CH2:23][CH2:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57548057HCID 57548057, compound

Product 1

HCID 25205716HCID 25205716, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of anhydrous THF (20 ml) containing 75A (0.42 g, 1.06 mmol) were added 3.18 ml (3 eq) of TBAF (1.0 M in THF) under N2. After the addition, the resulting solution was refluxed for 18 hours and subsequently concentrated in vacuo. Ethyl acetate was added and the organic layer was washed with a concentrated NaHCO3 solution, dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (MeOH), followed by a further purification on (25 g) SCX-2 (MeOH followed by 1 N NH3/MeOH) to afford the title compound 76A. (oil, 0.2 g, 73%). LCMS (Method A): Rt: 1.0 min, ([M+H]+=266). 1H-NMR (400 MHz, CDCl3): δ 7.54 (s, 1H), 6.36-6.31 (m, 1H), 3.49-3.46 (m, 2H), 2.75 (t, J=7 Hz, 2H), 2.64 (t, J=6 Hz, 2H), 2.47 (s, 3H), 2.43-2.38 (m, 2H), 1.55-1.49 (m, 2H), 1.35-1.23 (m, 4H), 0.85 (t, J=7 Hz, 3H).

Workup

  1. additionAfter the addition
  2. temperaturethe resulting solution was refluxed for 18 hours
  3. concentrationsubsequently concentrated in vacuo
  4. additionEthyl acetate was added
  5. washthe organic layer was washed with a concentrated NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by flash chromatography (MeOH)
  10. customfollowed by a further purification on (25 g) SCX-2 (MeOH followed by 1 N NH3/MeOH)

Sources & evidence

ORD record
ord-952b4852a5b94d1ba7b8397ed253f65e
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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