Methanol → HCID 15663629, compound

Participants

Reaction Steps

A solution of 5-ethynyl-1-azabicyclo[3.2.1]octane (D6) (1 g, 0.0074 mol) in tetrahydrofuran (5 ml) was treated with azidotrimethylsilane (1.27 g, 0.011 mol) at 140° C. for 8 h in a PTFE lined autoclave. The reaction was then cooled and treated with methanol (30 ml). The solution was then concentrated in vacuo to a brown gum. The gum was then taken up in methanol (30 ml) and treated with diazomethane in ether (excess) and allowed to stand for 15 min at 20° C. The reaction mixture was then concentrated in vacuo to a gum and chromatographed on neutral alumina in a gradient of 10-40% methanol in ethyl acetate. Elution with 15% methanol in ethyl acetate afforded the required product as a gum which slowly crystallised on standing. Recrystallisation from petrol afforded the title compound (EI, 99mg, 7%) as needles.

Provenance & Evidence