Imidazole → (1R*,2R*)-1,2,3,4-tetrahydro-1-(1H-imidazol-1-ylmethyl)-6-methoxy-2-(4-methoxyphenyl)naphthalene

HRID 1165511Notes

Reaction equation

HRID 1165511 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@H:9]([CH2:13]S(OC)(=O)=O)[C@H:8]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH2:7][CH2:6]2.[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:27]1([CH2:13][C@H:9]2[C:10]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=3)[CH2:6][CH2:7][C@H:8]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 86743813methyl (1R*,2R*)-1,2,3,4-tetrahydro-6-methoxy-2-(4-methoxyphenyl)-1-naphthylmethanesulphonate

Product 1

HCID 53804055(1R*,2R*)-1,2,3,4-tetrahydro-1-(1H-imidazol-1-ylmethyl)-6-methoxy-2-(4-methoxyphenyl)naphthalene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl (1R*,2R*)-1,2,3,4-tetrahydro-6-methoxy-2-(4-methoxyphenyl)-1-naphthylmethanesulphonate (1 g), imidazole (1.2 g) and potassium carbonate (1.2 g) in acetonitrile (75 ml) was stirred and heated under reflux for 24 h. The acetonitrile was evaporated under reduced pressure, and the residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml). The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate (50 ml). The combined ethyl acetate extracts were dried and evaporated to dryness, and the residue was purified by flash column chromatography on silica (K60), using ethyl acetate: toluene (1:4 by volume), then ethyl acetate as the eluting solvent, to give (1R*,2R*)-1,2,3,4-tetrahydro-1-(1H-imidazol-1-ylmethyl)-6-methoxy-2-(4-methoxyphenyl)naphthalene as a colourless gum, which crystallised on standing, m.p. 114°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 h
  3. customThe acetonitrile was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted twice with ethyl acetate (50 ml)
  7. dry with materialThe combined ethyl acetate extracts were dried
  8. customevaporated to dryness
  9. customthe residue was purified by flash column chromatography on silica (K60)

Sources & evidence

ORD record
ord-53c399381fd04ec09423308fa28a376e
Source dataset
uspto-grants-1990_03
Patent number
US04910212

Reaction notes

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