Ammonia → Thietan-3-amine

Participants

Reaction Steps

An autoclave was charged with 3-pyridinium-thietane p-toluenesulfonate (1 g) and ammonia in methanol (7M, 20 ml). The apparatus was closed and placed in a pre-heated oil bath at 180° C. for 30 min (pressure 15 bar). The reaction mixture was cooled to room temperature then in ice bath. The yellow solution was concentrated under reduced pressure to afford the title product alongside ammonium tosylate (800 mg, NMR ratio 1:2 thietanamine:ammonium tosylate). 1H-NMR (400 MHz, DMSO-d6): 3.18 (dt, 2H), 3.36 (br s, 2H), 3.41 (dt, 2H), 4.50 (quint., 1H).

Provenance & Evidence