HCID 20795053, compound → HCID 69658039, compound

HRID 585047Notes

Reaction equation

HRID 585047 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:17]([C:18](=O)[CH:19]=1)=[CH:16][CH:15]=[C:14]1[C:9]=2[CH:10]=[CH:11][CH:12]=[N:13]1)=[O:5])[CH3:2].[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:19][CH2:18][C:17]2[C:8](=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH2:12][CH2:11][CH2:10]3)[O:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 20795053HCID 20795053, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69658039HCID 69658039, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

8-Oxo-8H-5-oxa-1-aza-phenanthrene-6-carboxylic acid ethyl ester (2.0 g, 7.4 mmole) was dissolved in 200 mL of ethanol and 0.50 g of 20% palladium hydroxide on carbon added. The mixture was treated with 60 psi of hydrogen on a Parr apparatus for 48 hours, then filtered through celite and concentrated in vacuum. Thin layer chromatography on silica gel vs. a starting material standard indicated that the reaction was incomplete. The material was redissolved in 150 mL of acetic acid, 0.50 g of 20% palladium hydroxide on carbon added, and the mixture again treated with 60 psi of hydrogen for 48 hours. It was then filtered through celite, concentrated in vacuum and column chromatographed on silica gel with 2% ethanol in chloroform as eluant to give 0.80 g of 1,3,4,6,7,8-hexahydro-2H-5-oxa-1-aza-phenanthrene-6-carboxylic acid ethyl ester. 1H-NMR (CDCl3): doublet 6.65 δ (1H); doublet 6.1 δ (1H); multiplet 4.7 δ (1H); quartet 4.25 δ (2H); broad singlet 3.65 δ (1H); multiplet 3.2 δ (2H); multiplet 2.65 δ (4H); multiplet 2.2 δ (2H); multiplet 1.95 δ (2H); triplet 1.25 δ (3H).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuum
  3. dissolutionThe material was redissolved in 150 mL of acetic acid
  4. addition0.50 g of 20% palladium hydroxide on carbon added
  5. additionthe mixture again treated with 60 psi of hydrogen for 48 hours
  6. filtrationIt was then filtered through celite
  7. concentrationconcentrated in vacuum and column
  8. customchromatographed on silica gel with 2% ethanol in chloroform as eluant

Sources & evidence

ORD record
ord-3b78349bf1eb4754acb41fca6d0d9373
Source dataset
uspto-grants-2005_08
Patent number
US06930109B2

Reaction notes

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