Tetrabutylammonium Fluoride → HCID 22007325, compound

HRID 613015Notes

Reaction equation

HRID 613015 reaction equation
[O:1]=[C:2]1[CH:11]=[C:10]([C:12]([N:14]([CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C)C)[CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:35]1[CH:40]=[C:39]([C:41]2[C:50]3[C:45](=[CH:46][C:47]([O:53][CH3:54])=[C:48]([O:51][CH3:52])[CH:49]=3)[CH:44]=[C:43]([CH2:55][OH:56])[C:42]=2[CH2:57][OH:58])[CH:38]=[CH:37][N:36]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[O:1]=[C:2]1[CH:11]=[C:10]([C:12]([N:14]([CH2:25][CH2:26][OH:27])[CH2:15][CH2:16][OH:17])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:35]1[CH:40]=[C:39]([C:41]2[C:50]3[C:45](=[CH:46][C:47]([O:53][CH3:54])=[C:48]([O:51][CH3:52])[CH:49]=3)[CH:44]=[C:43]([CH2:55][OH:56])[C:42]=2[CH2:57][OH:58])[CH:38]=[CH:37][N:36]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15872374HCID 15872374, compound

Product 1

HCID 22007325HCID 22007325, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-{2-(2-oxo-4-bis(2-tert-butyldimethylsilyloxyethyl)aminocarbonyl-1,2-dihydroquinolin-1-yl]-4-pyridyl}-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (1.9 g) in tetrahydrofuran (20 ml) is added a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (2.8 ml) under ice-cooling, and the mixture is stirred at room temperature for one hour. After the reaction is complete, the mixture is concentrated under reduced pressure to remove the solvent, and to the resultant are added methylene chloride and an aqueous sodium hydrogen carbonate solution. The methylene chloride layer is separated, washed, dried, and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1~5:1), and triturated with ether to give 1-{2-(2-oxo-4-bis(2-hydroxyethyl)aminocarbonyl-1,2-dihydroquinolin-1-yl)-4-pyridyl}-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (0.68 g) which is listed in Table 7.

Workup

  1. temperaturecooling
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customto remove the solvent
  4. additionto the resultant are added methylene chloride
  5. customThe methylene chloride layer is separated
  6. washwashed
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=10:1~5:1)
  11. customtriturated with ether

Sources & evidence

ORD record
ord-d7bdebd48d3a41b3a0e477979a03be34
Source dataset
uspto-grants-1999_12
Patent number
US06005106

Reaction notes

Loading…