Reaktion #170055

Reaktionsgleichung

N-((7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)propane-1-sulfonamide

3-oxetanone

Trimethylsilyl cyanide

→

N-((8-Benzyl-7-(3-cyanooxetan-3-ylamino)-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)propane-1-sulfonamide

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated again at 210° C. for 2 minutes
2. 2
   Waschenwashed with 1 N NaOH (1×20 mL) and brine (1×20 mL)
3. 3
   ExtraktionThe organic extract
4. 4
   Sonstigewas collected
5. 5
   Sonstigedried on MgSO4
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   Sonstigeto give a brown oil
8. 8
   SonstigeThe residue was purified by flash-chromatography on silica gel (100% heptane

Vorschrift

N-((7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)propane-1-sulfonamide (0.104 g, 0.279 mmol) and 3-oxetanone (0.040 g, 0.558 mmol) were sealed in a vial and heated at 210° C. for 2 minutes. Trimethylsilyl cyanide (0.074 mL, 0.558 mmol) was added, the vial was resealed and the mixture was heated again at 210° C. for 2 minutes. The mixture was diluted with ethyl acetate (40 mL) and washed with 1 N NaOH (1×20 mL) and brine (1×20 mL). The organic extract was collected, dried on MgSO4 and evaporated under reduced pressure to give a brown oil. The residue was purified by flash-chromatography on silica gel (100% heptane then gradient to 60% ethyl acetate in n-heptane in 40 mins). (0.054 mg, 0.12 mmol, 43%).

Quelle