HCID 22182534, compound → HCID 22182528, compound

HRID 1070578Notes

Reaction equation

HRID 1070578 reaction equation
[NH:1]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][CH2:9][CH:8]([CH2:15][OH:16])[O:7]3)[CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[N:1]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][CH2:9][CH:8]([CH2:15][OH:16])[O:7]3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 22182534HCID 22182534, compound

Product 1

HCID 22182528HCID 22182528, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To (1,3,4,6,7,8-hexahydro-2H-5-oxa-1-aza-phenanthren-6-yl)-methanol (0.90 g, 4.0 mmole) in 150 mL of toluene was added 1.8 g (20 mmole) of manganese dioxide. The mixture was refluxed under nitrogen for 24 hours. It was then filtered through celite, concentrated in vacuum and column chromatographed on silica gel with 0-2% methanol/chloroform as eluant. Concentration of the product fractions in vacuum gave 0.30 g of the title compound as an orange oil. 1H-NMR (CDCl3): doublet 8.8 δ (1 H); doublet 8.4 δ (1 H); doublet 7.6 δ (1 H); doublet 7.35 δ (1 H); doublet of doublets 7.25 δ (1 H); multiplet 4.25 δ (1 H); multiplet 3.95 δ (2 H); multiplet 2.9 δ (2 H); multiplet 2.05 δ (2 H).

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 24 hours
  2. filtrationIt was then filtered through celite
  3. concentrationconcentrated in vacuum and column
  4. customchromatographed on silica gel with 0-2% methanol/chloroform as eluant

Sources & evidence

ORD record
ord-8c1896900f00428ab7e0a98e3d546782
Source dataset
uspto-grants-2005_06
Patent number
US06903110B2

Reaction notes

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