HCID 23369752, compound → HCID 23369712, compound

HRID 1900863Notes

Reaction equation

HRID 1900863 reaction equation
[N:1]([CH2:4][CH:5]1[O:21][C:8]2=[C:9]3[C:14](=[C:15](Br)[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-].[H][H]>CO.[Pd]>[NH2:1][CH2:4][CH:5]1[O:21][C:8]2=[C:9]3[C:14](=[CH:15][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 2

HCID 23369752HCID 23369752, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23369712HCID 23369712, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Azidomethyl-5-bromo-9,9-dimethyl-2,3,6,7,8,9-hexahydrofuro[2,3-f]quinoline-7-one (997 mg, 2.84 mmol) was dissolved in methanol (50 ml). To the solution, 10% palladium-on-carbon (1.0 g) was added, followed by stirring in a bath at 50° C. for 1 hour in the atmosphere of hydrogen. The catalyst was filtered off, and the filtrate was condensed under reduced pressure. Recrystallization from a solvent mixture of methanol-ether yielded 560 mg of the title compound as a yellow powder (80.4%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customcondensed under reduced pressure
  3. customRecrystallization
  4. additionfrom a solvent mixture of methanol-ether

Sources & evidence

ORD record
ord-23fe25c202ca4179aa423a553153e50d
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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