ethyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 36.6 g of 8-azabicyclo[3,2,1]octan-3-one-8-carboxylic acid ethyl ester (e) are dissolved in 500 ml of absolute petroleum ether, and 52.8 g of pyrrolidine are added. A solution of 19.4 g of titanium tetrachloride in 100 ml of petroleum ether is added dropwise within 70 minutes, with vigorous stirring. With slight warming of the solution, a light-yellow precipitate is immediately precipitated. After 110 hours' stirring at roomtemperature, the precipitate is allowed to settle and the yellow petroleum ether solution is decanted. The precipitate is suspended in 250 ml of anhydrous benzene, suction filtered, and washed with benzene. The united organic phases are concentrated in a vacuum; the oil which remains behind is purified by vacuum distillation to obtain 42.8 g (92.2 percent) of (d) as a light-yellow, viscous oil (b.p. 125° to 128° C. at 8 Pa.). With slight warming of the solution a light-yellow precipitate is immediately precipitated the yellow petroleum ether solution is decanted suction filtered washed with benzene The united organic phases are concentrated in a vacuum the oil which remains behind is purified by vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 186.8 g of pseudo-pelletierine and 264 g of freshly distilled chloroformic acid ethyl ester are slowly heated to a boil in 1 liter of absolute toluene within one hour. A vigorous evolution of gas sets in. The mixture is heated to a boil under reflux for a further 16 hours, then cooled and filtered. The filtrate is concentrated in a vacuum, and the residue is purified through vacuum distillation to obtain 223 g (86.5 percent) of light-yellow oil (b.p. 101° C. at 2.7 Pa.) The mixture is heated to a boil under reflux for a further 16 hours cooled filtered The filtrate is concentrated in a vacuum the residue is purified through vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, under a nitrogen atmosphere and with stirring, a solution of 110 g of titanium tetrachloride in 450 ml of petroleum ether is added dropwise, within 2.5 hours, to a solution of 223 g of 9-azabicyclo-[3,3,1]nonan-3-one-9-carboxylic acid ethyl ester (e) and 300 g of pyrrolidine in 2.5 liters of absolute petroleum ether (b.p. 50° to 70° C.). The mixture is stirred for 24 hours. The light-yellow precipitate formed is filtered, suspended in benzene, suctionfiltered and washed with benzene. The united filtrates are concentrated in a vacuum; the orange-red oil which remains behind is purified through vacuum distillation to obtain 260 g (93.5 percent) of yellow, viscous oil (b.p. 140° C. at 6.7 Pa.) The mixture is stirred for 24 hours The light-yellow precipitate formed is filtered washed with benzene The united filtrates are concentrated in a vacuum the orange-red oil which remains behind is purified through vacuum distillation to obtain 260 g (93.5 percent) of yellow, viscous oil (b.p. 140° C. at 6.7 Pa.)