HCID 15663627, compound → 5-Ethynyl-1-azabicyclo[3.2.1]octane

Participants

Reaction Steps

A solution of crude (±) 5-(2,2-dibromoethenyl)-1-azabicyclo[3.2.1]octane (10 g, 34 mM) (D5) in dry THF (200 ml) was cooled to -78° C. under nitrogen and treated with n-butyl lithium in hexane (49 ml of a 1.6 molar solution, 0.078 mol). The solution was stirred at this temperature for 1 h and then allowed to warm to room temperature over a period of 1 h. The reaction mixture was then cooled to -70° C. and quenched by the addition of acetic acid (10 ml). The solution was then concentrated in vacuo to a gum and the residue partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried (Na2SO4) and concentrated in vacuo to a gum which was distilled in vacuo to afford the title compound (D6, 2.5 g, 51%) as a colourless oil (B.pt 110°-120° at 0.5 mM) which crystallised on standing m.p. 41°-42° C.

Provenance & Evidence