Réaction #76165

Équation de réaction

tert-butyl 3-[(methylsulfonyl)oxy]-1-azetidinecarboxylate

potassium iodide

→

title compound

tert-Butyl 3-iodo-1-azetidinecarboxylate

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe cooled mixture was partitioned between water and ethyl acetate
2. 2
   Autrethe layers separated
3. 3
   SéchageThe organic phase was dried over MgSO4
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   Autrethe residue azeotroped with xylene
6. 6
   AutreThe crude product was purified by flash column chromatography (dichloromethane as eluant)

Mode opératoire

A mixture of tert-butyl 3-[(methylsulfonyl)oxy]-1-azetidinecarboxylate (prepared as described in Synlett 1998, 379; 5.0 g, 19.9 mmol), and potassium iodide (16.5 g, 99.4 mmol) in N,N-dimethylformamide (25 mL), was heated at 100° C. for 42 h. The cooled mixture was partitioned between water and ethyl acetate, and the layers separated. The organic phase was dried over MgSO4, concentrated under reduced pressure and the residue azeotroped with xylene. The crude product was purified by flash column chromatography (dichloromethane as eluant) to give the title compound, 3.26 g.

Source