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

Participants

Reaction Conditions

Reaction Steps

N-((7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)-1-cyclopropylmethanesulfonamide (0.083 g, 0.216 mmol) and 3-oxetanone (0.031 g, 0.432 mmol) were sealed in a vial and heated at 200° C. for 2 minutes. Trimethylsilyl cyanide (0.58 mL, 0.432 mmol) was added, the vial was resealed and the mixture was heated again at 200° C. for 2 minutes. The mixture was diluted with ethyl acetate (40 mL) and washed with 1N 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 up to 60% ethyl acetate in n-heptane). (24.9 mg, 0.048 mmol, 22.3%).

Provenance & Evidence