Reaktion #74447

Reaktionsgleichung

t-BuOH

5-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate

Et3N

Diphenylphosphorylazide

→

title compound

tert-butyl {[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]methyl}carbamate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 95° C. overnight
2. 2
   TemperaturAfter cooling to room temperature the reaction mixture
3. 3
   Filtrationwas filtered through a pad of celite
4. 4
   WaschenThe celite pad was washed thoroughly with CH2Cl2
5. 5
   Einengenwere concentrated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
7. 7
   Waschenthe organic layer was washed with half-saturated aqueous NaHCO3 solution (1×)
8. 8
   Trocknendried over Na2SO4
9. 9
   Einengenconcentrated

Vorschrift

A mixture of 5-(4-bromophenyl)-5-(carboxymethyl)-5H-imidazo[2,1-a]isoindol-1-ium trifluoroacetate (1.27 g), Et3N (0.989 mL) and 4 Angstrom powdered molecular sieves in t-BuOH (10 mL) was stirred for 20 minutes at room temperature. Diphenylphosphorylazide was then added to this mixture and heated at 95° C. overnight. After cooling to room temperature the reaction mixture was filtered through a pad of celite. The celite pad was washed thoroughly with CH2Cl2, combined washings and filtrate were concentrated. The residue was dissolved in CH2Cl2 and the organic layer was washed with half-saturated aqueous NaHCO3 solution (1×), dried over Na2SO4 and concentrated. Flash chromatography using a linear gradient of 3% EtOAc/0% MeOH to 50% EtOAc/2% MeOH in hexanes afforded title compound as a white solid. Mass. found (M+H)+, 442.0.

Quelle