Trimethylsilyl cyanide → N-(3-cyanooxetan-3-yl)-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

To a yellow solution of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (1 g, 5.71 mmol) in CH2Cl2 (20 ml) in a 100 round-bottomed flask was added titanium tetraethoxide (0.651 g, 2.85 mmol) and the reaction mixture stirred for 10 min. TMSCN (1.530 ml, 11.41 mmol) was then added, and the resulting reaction mixture stirred at r.t. for overnight. The reaction mixture was poured into saturated brine solution, and then the suspension was filtered through a pad of Celite. The organic layer was separated, and the aqueous layer extracted with ethyl acetate (3×25 ml). The combined organic solution was washed with saturated brine solution, dried over Na2SO4, filtered and concentrated. The crude product was purified over neutral alumina column using 4% methanol in dichloromethane as eluent. Desired fractions were collected and concentrated to give the titled product as colorless oil (0.9 g, 78%).

Provenance & Evidence