Triphenylphosphine → HCID 23369608, compound

HRID 1900864Notes

Reaction equation

HRID 1900864 reaction equation
[N:1]([CH2:4][CH:5]1[O:21][C:8]2=[C:9]3[C:14](=[C:15]([Br:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[CH2:11][C:10]3([CH3:20])[CH3:19])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>O1CCCC1>[NH2:1][CH2:4][CH:5]1[O:21][C:8]2=[C:9]3[C:14](=[C:15]([Br:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[CH2:11][C:10]3([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 23369752HCID 23369752, compound

Product 1

HCID 23369608HCID 23369608, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2-Azidomethyl-5-bromo-9,9-dimethyl-2,3,6,7,8,9-hexahydrofuro[2,3-f]quinoline-7-one (492 mg, 1.40 mmol) was dissolved in tetrahydrofuran (10 ml). To the solution, triphenylphosphine (404 mg, 1.54 mmol) was added, and the mixture was stirred in a bath at 50° C. for 2 hours. After completion of the reaction, aqueous 2N-caustic soda solution (2 ml) was added to the reaction mixture, followed by stirring a further 1 hour at room temperature. The reaction mixture was condensed under reduced pressure, and extracted with chloroform and 2N-HCl. The aqueous phase was neutralized with aqueous 2N-caustic soda solution, and then extracted with a solvent mixture of chloroform-methanol (10:1), dried, and condensed under reduced pressure. The condensate was purified by silica gel column chromatography (developer=chloroform). Recrystallization from chloroform-methanol-ether yielded 330 mg of the title compound as pale yellow needles (72.1%).

Workup

  1. additionwas added to the reaction mixture
  2. stirringby stirring a further 1 hour at room temperature
  3. customcondensed under reduced pressure
  4. extractionextracted with chloroform and 2N-HCl
  5. extractionextracted with a solvent mixture of chloroform-methanol (10:1)
  6. customdried
  7. customcondensed under reduced pressure
  8. customThe condensate was purified by silica gel column chromatography (developer=chloroform)
  9. customRecrystallization from chloroform-methanol-ether

Sources & evidence

ORD record
ord-edfdacb13ccc4b18b988aa657e301bd2
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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