반응 #74447

반응 방정식

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

반응 조건

후처리

1. 1
   온도heated at 95° C. overnight
2. 2
   온도After cooling to room temperature the reaction mixture
3. 3
   여과was filtered through a pad of celite
4. 4
   세척The celite pad was washed thoroughly with CH2Cl2
5. 5
   농축were concentrated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
7. 7
   세척the organic layer was washed with half-saturated aqueous NaHCO3 solution (1×)
8. 8
   건조dried over Na2SO4
9. 9
   농축concentrated

실험 절차

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.

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