Diethylamine → 3-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]-3-methylbutan-1-ol

HRID 76903

Reaktionsgleichung

Reaktionsgleichung von HRID 76903
[Si]([O:8][CH2:9][CH2:10][C:11]([C:14]1[N:15]=[CH:16][N:17](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=1)([CH3:13])[CH3:12])(C(C)(C)C)(C)C.[Br:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH2:41]Br.C(NCC)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>CC#N.CO>[Br:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH2:41][N:15]1[C:14]([C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][OH:8])=[CH:18][N:17]=[CH:16]1

Komponenten

8

Edukt 5

HCID 8021DiethylamineHCID 769652-Bromobenzyl bromideHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 536308684-[3-(tert-butyldimethylsilanyloxy)-1,1-dimethylpropyl]-1-trityl-1H-imidazole

Produkt 1

HCID 588271963-[3-(2-Bromobenzyl)-3H-imidazol-4-yl]-3-methylbutan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-[3-(tert-butyldimethylsilanyloxy)-1,1-dimethylpropyl]-1-trityl-1H-imidazole (650 mg, 1.27 mmol) in CH3CN (10 mL) at ambient temperature is added a solution of 2-bromobenzyl bromide (420 mg, 1.68 mmol) in CH3CN (10 mL). The resulting solution is stirred at 80° C. for 6 h. The mixture is cooled to ambient temperature and diethylamine (2 mL) is added, followed by MeOH (10 mL) and the mixture is heated at 75° C. for 1 hr and stirred at ambient temperature overnight. To the reaction mixture is added HCl/dioxane (4 M, 5 mL, 20 mmol) and stirred at ambient temperature for 1 h. The mixture is neutralized with saturated aqueous NaHCO3 and concentrated. The residue is partitioned between CH2Cl2 and brine. The organic layer is washed with brine, dried over Na2SO4 and concentrated to give an oil, which is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 323 (M+H).

Aufarbeitung

  1. temperatureThe mixture is cooled to ambient temperature
  2. temperaturethe mixture is heated at 75° C. for 1 hr
  3. stirringstirred at ambient temperature overnight
  4. stirringstirred at ambient temperature for 1 h
  5. concentrationconcentrated
  6. customThe residue is partitioned between CH2Cl2 and brine
  7. washThe organic layer is washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customto give an oil, which
  11. washeluting with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-562c9b54bf2843f58f5b7b908d5f5023
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835646B2

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