Hydrochloric Acid → HCID 19018591, compound

Participants

Reaction Steps

(±) 5-(α-Bromoacetyl) -1-azabicyclo[3.2.11octane hydrobromide (1.0 g, 3.2 mmol) was converted into (±) 2-oxo-2-(1-azabicyclo[3.2.1 ]oct-5-yl) ethanal hydrobromide as described in Example 1. The crude aldehyde was immediately treated with a suspension of aminoguanidine bicarbonate (0.46 g, 3.38 mmol) in water (15 ml) and the solution was acidified to pH4 with 5M HCl. After stirring overnight at room temperature the reaction mixture was saturated with potassium carbonate then extracted into chloroform. The combined organic extracts were dried over sodium sulphate, concentrated in vacuo and the residue chromatographed on neutral alumina in a gradient of 0-8% methanol in chloroform. This afforded the title compound (E2) as a solid (95 mg, 15%) which was converted into the oxalate salt m.p. 184° C. (dec) (from methanol-ether)..

Provenance & Evidence