Reaktion #543956

Reaktionsgleichung

methyl (1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

1,3-diiodo-5,5-dimethylhydantoin

acetic acid

→

compound

Methyl (1S,3S,4S,6R,7S)-6-acetyloxy-7-iodo-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe solution was concentrated under reduced pressure
2. 2
   workup.ADDITIONThe resulting mixture was diluted with ethyl acetate
3. 3
   Waschenwashed successively with sodium hydrogencarbonate solution, sodium thiosulfate solution, sodium hydrogen carbonate solution and brine
4. 4
   TrocknenThe organic layer was dried over MgSO4
5. 5
   Sonstigeevaporated in vacuo

Vorschrift

To a solution of methyl (1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate obtained in Example 42-2 (1.0 g) in acetic acid (9 mL), was added portionwise 1,3-diiodo-5,5-dimethylhydantoin (782 mg). The mixture was stirred at room temperature for 30 minutes. The solution was concentrated under reduced pressure. The resulting mixture was diluted with ethyl acetate, and washed successively with sodium hydrogencarbonate solution, sodium thiosulfate solution, sodium hydrogen carbonate solution and brine. The organic layer was dried over MgSO4 and evaporated in vacuo to give the target compound as a solid (1.74 g).

Quelle