Formic Acid → HCID 18960867, compound

HRID 257453Notes

Reaction equation

HRID 257453 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[C:8]([C:15]1[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][N:16]=1)=[C:9](Cl)[CH2:10]2)=[O:5])[CH3:2].C(N(CC)CC)C.C(O)=O>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[C:8]([C:15]1[CH:19]=[C:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:17][N:16]=1)=[CH:9][CH2:10]2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 18960912HCID 18960912, compound

Product 1

HCID 18960867HCID 18960867, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.3 g (3.6 mmol) 8-ethoxycarbonyl-3-chloro-2-(5-phenyl-3-isoxazolyl)-8-azabicyclo[3.2.1]oct-2-ene was dissolved in 30 ml ethanol. 300 mg Pd/C 5%, triethylamine (7 ml) and formic acid (3 ml) was added and the reaction mixture heated at reflux for 4 h. The mixture was concentrated in vacuo, water (50 ml) was added and the solution extracted with ethylether 3×20 ml. The organic phase was dried over magnesiumsulphate and concentrated in vacuo. The crude product was purified by column chromatography with methylenchloride/ethylacetate (9:1) as eluent. Yield 600 mg oil.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 4 h
  3. concentrationThe mixture was concentrated in vacuo, water (50 ml)
  4. additionwas added
  5. extractionthe solution extracted with ethylether 3×20 ml
  6. dry with materialThe organic phase was dried over magnesiumsulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography with methylenchloride/ethylacetate (9:1) as eluent

Sources & evidence

ORD record
ord-541760d9624d487796f1bf77b2778cb8
Source dataset
uspto-grants-1993_11
Patent number
US05262427

Reaction notes

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