To a suspension of 2-(formyl-3-methoxyphenoxy)ethyl polystyrene (AMEBA) resin (ex Novabiochem) (6.85 g, 3.33 mmol) in a mixture of methanol/dichloromethane (60 ml, 1:1 v/v) is added 2-amino ethanol and sodium triacetoxyborohydride (4.00 g, 18.85 mmol) and the mixture shaken for 16 hours at 20° C., then filtered. The resin is washed with methanol, DMF and dichloromethane, then dried under vacuum. A THF/acetonitrile mixture (50 ml, 1:1 v/v) is added to the dried resin followed by iodine (4.80 g, 18.85 mmol), imidazole (1.28 g, 18.85 mmol) and triphenylphosphine (4.90 g,18.85 mmol). The suspension obtained is shaken for 18 hours at 20° C., then filtered. The resin is washed with THF and dried under vacuum. To the freshly prepared resin (0.50 g, 0.35 mmol) is added a solution of (4-chloro-phenyl)-piperidin-4-yl-methanone hydrochloride (0.18 g, 0.70 mmol) dissolved in DMF (2 ml) and diisopropylethylamine (0.36 g, 2.8 mmol). The mixture is heated at 50° C. for 16 hours and then filtered. The resin is washed with DMF. To the washed resin are added (E)-3-(5-Bromo-2-methoxy-phenyl)-acrylic acid (0.27 g, 1.05 mmol), 2-(1H benzotriazol-1-yl)-1,1,3,3,-tetramethyluronium tetrafluoroborate (0.34 g, 1.05 mmol), diisopropylethylamine (0.29 g, 1.05 mmol) and DMF (4 ml) and the mixture is shaken at 20° C. for 16 hours, then washed with DMF and methanol, after which it is treated with trifluoroacetic acid/dichloromethane (6 ml, 1:1 v/v) at 20° C. for 1 hour to remove the product from the resin. The resulting mixture is filtered and the filtrate evaporated under vacuum to give the product, [MH]+506.7.
