Pyrrolidine → 3-(1-Pyrrolidinyl)-9-azabicyclo[3,3,1]non-2-ene-9-carboxylic acid ethylester
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH2:14][CH:7]1[CH2:8][C:9](=O)[CH2:10]2)=[O:5])[CH3:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH2:14][CH:7]1[CH:8]=[C:9]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:10]2)=[O:5])[CH3:2]Participants
4
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.)