Iodine → HCID 11857597, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium borohydride (0.05 g, 1.21 mmol, 2.4 eq) in tetrahydrofuran (0.5 ml) is added a solution of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-4-(2-oxo-2-pyrrolidin-1-ylethyl)-1,3-oxazole 52 (0.2 g, 0.5 mmol, 1 eq) in tetrahydrofuran (2 ml). The mixture is cooled down to 0° C. (ice bath) and a solution of iodine (0.13 g, 0.5 mmol, 1 eq) in tetrahydrofuran (1 ml) is added dropwise. When the release of gas has stopped, the mixture is heated to reflux overnight. Methanol is added to the mixture at 0° C. until complete dissolution. The solvent is removed under vacuum to give a white solid. The solid is taken up into a 20% methanolic solution of potassium hydroxide and the mixture is heated at 60° C. for 10 h. The mixture is poured onto water and extracted with dichloromethane. The organic layer is dried over magnesium sulfate and the solvent is removed in vacuum. The crude product is purified by chromatography over silica gel (eluent: gradient of dichloromethane/methanol/ammonia) to give 0.03 g of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole 55 as an orange oil.

Provenance & Evidence