Cesium carbonate → 4-Benzyloxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Participants

Reaction Steps

A mixture of 13.0 g (64.6 mmol) 4-benzyloxy-1H-pyridin-2-one, 23.7 g (90.4 mmol) [4-(2-iodoethyl)-phenyl]-methanol (preparation 1b) and 63.1 g (194 mmol) cesium carbonate in 55 mL of DMF is stirred overnight at RT. The reaction mixture is heated to 70° C., filtered through a pad of celite which is washed with hot DMF. The solvent is removed almost completely. After cooling to RT, MeOH is added, the precipitate is filtered, washed with EtOAc and water and is dried in vacuo at 40° C. (fraction A). MeOH is removed in vacuo, the residue is redissolved in DMF and purified by reverse HPLC (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile 95:5 to 10:90) to give fraction B, which is combined with fraction A.

Provenance & Evidence