Sodium Iodide → (R)-1-[3-(tert-Butoxycarbonyl-methyl-amino)-propyl]-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane chloride

Participants

Reaction Conditions

Reaction Steps

(3-Chloro-propyl)-methyl-carbamic acid tert-butyl ester (2.00 g 9.629 mmol) is solubilised in DMF (20 ml) and polystyrene bound DIPEA added, and after a few minutes removed. This solution is then added to a mixture of hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo [2.2.2]oct-3-yl) ester (2.1634 g 6.419 mmol) and 200 mg of K2CO3, followed by the addition of sodium iodide (10 mg) and heating at 60° C. for 2 days. 2.5 g Merrifield resin and 100 mg K2CO3 is then added to the mixture and heating resumed at 40° C. for 12 hours. The resin is then removed, and the mixture purified by gradient C18 column chromatography to give the title product.

Provenance & Evidence