HCID 70224214, compound → HCID 21186765, compound

HRID 1384272Notes

Reaction equation

HRID 1384272 reaction equation
[H][H].[CH3:3][O:4][C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:15])[N+:8]([O-])=[C:7]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:6]=12>CO>[CH3:3][O:4][C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:15])[N:8]=[C:7]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:6]=12

Participants

4

Reactant 2

HCID 70224214HCID 70224214, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21186765HCID 21186765, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methanol (5.0 ml) was added to Raney nickel water suspension (0.2 ml) and stirred at room temperature for 30 minutes in an atmosphere of hydrogen. The reaction solution was mixed with methanol solution (6.0 ml) of methyl 4-methoxy-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (607.9 mg, 2.29 mmol) and stirred at room temperature for 30 hours in an atmosphere of hydrogen. After removal of the catalyst by filtration, the resulting residue was washed with methanol, the solvent was evaporated under reduced pressure, and the thus obtained residue was dissolved in ethyl acetate and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1) to obtain the title compound (567.8 mg, 99.6%) as colorless oil.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. washthe resulting residue was washed with methanol
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionthe thus obtained residue was dissolved in ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporation of the solvent under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1)

Sources & evidence

ORD record
ord-4c98a8d202264709ad4ff5c5db5c4e5d
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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