HCID 22182534, compound → HCID 22182528, compound

HRID 1796701Notes

Reaction equation

HRID 1796701 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-d8b60662c4374d1e8b881a534df0e76a
Source dataset
uspto-grants-2006_04
Patent number
US07030245B2

Reaction notes

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