[Br-].C([N+:9]12[CH2:17][C:13]([C:18]([O:20]CC)=[O:19])([CH2:14][CH2:15][CH2:16]1)[CH2:12][CH2:11][CH2:10]2)C1C=CC=CC=1.[H][H].[ClH:25]>C(O)C.[Pd]>[ClH:25].[N:9]12[CH2:17][C:13]([C:18]([OH:20])=[O:19])([CH2:14][CH2:15][CH2:16]1)[CH2:12][CH2:11][CH2:10]2
A solution of ethyl 1-benzyl-1-azoniabicyclo[3.3.1]-non-5-ylcarboxylate bromide (D2, 7.90 g, 0.021 mole) in ethanol (150 ml) was hydrogenated over 10% Pd/C (700mg) at atmospheric pressure and 40° C. until the uptake of hydrogen ceased. The reaction mixture was filtered through a pad of kieselguhr and the filtrate concentrated in vacuo to leave a yellow solid, which was treated with 8M hydrochloric acid (130 ml) and heated under reflux until TLC indicated that hydrolysis was complete. The solution was concentrated to dryness in vacuo to give the title compound (D14) as a yellow solid (4.8 g), which was used in the next stage without purification.
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