Reaktion #76165

Reaktionsgleichung

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

potassium iodide

→

title compound

tert-Butyl 3-iodo-1-azetidinecarboxylate

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle