Reaktion #6045

Reaktionsgleichung

product

N-t-butyloxycarbonyl-1-aminomethyl-3-methylenecyclobutane

methanol

→

title compound

N-t-Butoxycarbonyl-3-aminomethylcyclobutanone

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a round bottom flask were placed
2. 2
   Sonstigeozone was bubbled through the reaction mixture until the solution
3. 3
   SonstigeThe system was flushed with nitrogen for 2.5 h
4. 4
   workup.ADDITIONtreated with 34 mL of dimethylsulide
5. 5
   workup.WAIT0° C. for 1 h
6. 6
   workup.WAITroom temperature for 1 h
7. 7
   workup.WAITthe solution was stored in a refrigerator at 5° C. overnight
8. 8
   Einengenbefore being concentrated
9. 9
   SonstigeThe crude material was purified by column chromatography

Vorschrift

In a round bottom flask were placed 9 g of the product from Step A of Example 9, 100 mL of methanol, and 400 mL of dichloromethane. The solution was cooled to -78° C., and ozone was bubbled through the reaction mixture until the solution was blue. The system was flushed with nitrogen for 2.5 h, and then treated with 34 mL of dimethylsulide. After 1 h at -78° C., 0° C. for 1 h, and room temperature for 1 h, the solution was stored in a refrigerator at 5° C. overnight before being concentrated. The crude material was purified by column chromatography to afford the title compound.

Quelle