Tetrabutylammonium Fluoride → HCID 178436670, compound

HRID 76266Notes

Reaction equation

HRID 76266 reaction equation
[CH2:1]([C:5]1=[CH:6][N:7]([C:27]([CH3:30])([CH3:29])[CH3:28])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:26])[C:12]1[CH:17]=[C:16]([C:18]#[C:19][Si](C)(C)C)[CH:15]=[CH:14][C:13]=1[O:24][CH3:25])[CH2:2][CH2:3][CH3:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[CH2:1]([C:5]1=[CH:6][N:7]([C:27]([CH3:28])([CH3:30])[CH3:29])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:26])[C:12]1[CH:17]=[C:16]([C:18]#[CH:19])[CH:15]=[CH:14][C:13]=1[O:24][CH3:25])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178441282HCID 178441282, compound

Product 1

HCID 178436670HCID 178436670, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 62A (300 mg, 0.68 mmol) in THF (10 mL) was treated with TBAF (1M) (1.7 mL, 1.7 mmol), stirred at rt for 1 hr, diluted with H2O and extracted with EtOAc (2×). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 183 mg (73%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 0.98 (t, J=7.36 Hz, 3 H) 1.36-1.50 (m, 2 H) 1.65 (s, 9 H) 1.67-1.77 (m, 2 H) 2.83 (dd, J=7.98 Hz, 2 H) 2.99 (s, 1 H) 3.94 (s, 3 H) 6.93 (d, J=8.59 Hz, 1 H) 7.52 (dd, J=8.59, 2.15 Hz, 1 H) 7.93 (s, 1 H) 8.28 (d, J=2.15 Hz, 1 H); MS (DCI/NH4+) m/z 371 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9087fc0356e148dcb84628d801ace58b
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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