4-Methyl-1-trityl-1H-imidazole → (1R*,2R*)-1,2,3,4-tetrahydro-6-methoxy-2-(4-methoxyphenyl)-1-(5-methylimidazol-1-ylmethyl)naphthalene

HRID 1165515Notes

Reaction equation

HRID 1165515 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.C([N:46]1[CH:50]=[C:49]([CH3:51])[N:48]=[CH:47]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@H:9]([CH2:13][N:48]1[C:49]([CH3:51])=[CH:50][N:46]=[CH:47]1)[C@H:8]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 6182544-Methyl-1-trityl-1H-imidazoleHCID 86743813methyl (1R*,2R*)-1,2,3,4-tetrahydro-6-methoxy-2-(4-methoxyphenyl)-1-naphthylmethanesulphonate

Product 1

HCID 54255105(1R*,2R*)-1,2,3,4-tetrahydro-6-methoxy-2-(4-methoxyphenyl)-1-(5-methylimidazol-1-ylmethyl)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 (0.2 g) and 1-trityl-4-methylimidazole (0.172 g) in acetonitrile (10 ml) was stirred and heated under reflux for 72 h. The acetonitrile was evaporated under reduced pressure, and the residue was dissolved in 90% by volume aqueous acetic acid (20 ml). This acetic acid solution was heated under reflux for 24 h, and then evaporated to dryness under reduced pressure, and the residue was dissolved in a mixture of ethylacetate (25 ml) and water (25 ml). The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate (40 ml). The combined ethyl acetate solutions were dried and evaporated to dryness, and the residue was purified by flash column chromatography on silica (K60), using methanol/dichloromethane, 2:98 by volume, then methanol/dichloromethane, 5:95 by volume, as the eluting solvent, to give (1R*,2R*)-1,2,3,4-tetrahydro-6-methoxy-2-(4-methoxyphenyl)-1-(5-methylimidazol-1 -ylmethyl)naphthalene as a colourless gum. Nmr in CDCl3 : δ 7.25(2H, d); 6.95(3H, m); 6.7(2H, m); 6.5(1H, dd); 5.95(1H, d); 3.85(3H, s); 3.8(3H, s); 3.65(2H, m); 3.3(1H, m); 3.05(3H, m); 2.15(2H, m); 1.65 (3H, s).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 72 h
  3. customThe acetonitrile was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in 90% by volume aqueous acetic acid (20 ml)
  5. temperatureThis acetic acid solution was heated
  6. temperatureunder reflux for 24 h
  7. customevaporated to dryness under reduced pressure
  8. dissolutionthe residue was dissolved in a mixture of ethylacetate (25 ml) and water (25 ml)
  9. customThe organic layer was separated
  10. extractionthe aqueous layer was extracted twice with ethyl acetate (40 ml)
  11. dry with materialThe combined ethyl acetate solutions were dried
  12. customevaporated to dryness
  13. customthe residue was purified by flash column chromatography on silica (K60)

Sources & evidence

ORD record
ord-7b1b0a5920f742ee80e356fd43ff8565
Source dataset
uspto-grants-1990_03
Patent number
US04910212

Reaction notes

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