Reacción #74447

Ecuación de reacción

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

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated at 95° C. overnight
2. 2
   TemperaturaAfter cooling to room temperature the reaction mixture
3. 3
   Filtraciónwas filtered through a pad of celite
4. 4
   LavadoThe celite pad was washed thoroughly with CH2Cl2
5. 5
   Concentraciónwere concentrated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
7. 7
   Lavadothe organic layer was washed with half-saturated aqueous NaHCO3 solution (1×)
8. 8
   Secadodried over Na2SO4
9. 9
   Concentraciónconcentrated

Procedimiento

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.

Fuente