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

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Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence