Water → HCID 67771149, compound

HRID 1900800Notes

Reaction equation

HRID 1900800 reaction equation
[Si]([O:8][CH2:9][CH:10]1[C:22]2[C:13](=[C:14]3[C:19](=[C:20]([CH3:23])[CH:21]=2)[NH:18][C:17](=[O:24])[CH:16]=[CH:15]3)[O:12][CH:11]1[CH2:25][N:26](CC=C)CC=C)(C(C)(C)C)(C)C.N12CCN(CC1)CC2.O>O1CCCC1.CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)C.C(Cl)(Cl)Cl.CO>[NH2:26][CH2:25][CH:11]1[O:12][C:13]2=[C:14]3[C:19](=[C:20]([CH3:23])[CH:21]=[C:22]2[CH:10]1[CH2:9][OH:8])[NH:18][C:17](=[O:24])[CH:16]=[CH:15]3

Participants

9

Reactant 3

HCID 962WaterHCID 9237DabcoHCID 67771160HCID 67771160, compound

Product 1

HCID 67771149HCID 67771149, compoundYield 43.4%

Reagents, catalysts & solvents 5

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

(2RS,3SR)-3-(tert-Butyldimethylsilyloxy)methyl-2-diallylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.17 g, 4.62 mmol) was dissolved in a solvent mixture (60 ml) of tetrahydrofuran--N,N-dimethylformamide (5:1), to which tetra-n-butylammonium chloride (1.0 M tetrahydrofuran solution, 10 ml, 10.0 mmol) was added, followed by stirring at room temperature for 8 hours. The reaction mixture was condensed under reduced pressure, and the resultant residue was separated by silica gel column chromatography (chloroform--methanol =50:1). All the fractions that contain spots in the vicinity of Rf=0.4 were collected, and condensed under reduced pressure. The resultant residue was dissolved in ethanol (100 ml). To the solution, Wilkinson catalyst (140.0 mg, 0.15 mmol), 1,4-diazabicyclo[2,2,2]octane (200.0 mg, 1.78 mmol) and water (10 ml) were added, and the mixture was refluxed with heat for 2 hours. The reaction mixture was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: saturated ammonia--methanol=50:1). Crude crystals were obtained (500 The crude crystals were dissolved in a solvent mixture of chloroform and methanol (4:1), to which 4N-HCl--dioxane (0.6 ml, 2.40 mmol) was added. The resultant mixture was condensed under reduced pressure, then subjected to azeotropic distillation along with methanol (twice). The residue was recrystallized from methanol--ether. 521.7 mg of the title compound was obtained as pale yellow powdery crystals (38.1%).

Workup

  1. additionwas added
  2. customcondensed under reduced pressure
  3. customthe resultant residue was separated by silica gel column chromatography (chloroform--methanol =50:1)
  4. customwere collected
  5. customcondensed under reduced pressure
  6. temperaturethe mixture was refluxed
  7. temperaturewith heat for 2 hours
  8. customcondensed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform: saturated ammonia--methanol=50:1)
  10. customCrude crystals were obtained (500 The crude crystals
  11. additionwas added
  12. customcondensed under reduced pressure
  13. distillationsubjected to azeotropic distillation along with methanol (twice)
  14. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-3d47be9d08b542c39d43b1f886e95393
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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