Patent ID: 8703802
Filing Date: 2014-04-22
Classification: C07C,C07D

Abstract:
1. A process for the preparation of (2S)-(4E)-N-methyl-5-[3-(5-isopropoxypyridin)yl]-4-penten-2-amine comprising: a) preparing (2S)-N-(tert-butoxycarbonyl)-N-methyl-4-penten-2-amine by a process comprising: b) mixing (2S)-N-(tert-butoxycarbonyl)-N-methyl-4-penten-2-amine (1 mole-equivalent) and 5-bromo-3-alkoxypyridine (1.1 mole-equivalents) with a palladium source (0.01 mole-equivalents), a phosphine ligand (0.24 mole-equivalents) and a base (1.5 mole-equivalents) in a suitable organic solvent under an atmosphere of nitrogen; c) adding water and heating the mixture to 90° C. for 15 to 25 h; d) cooling the mixture and adding water and an acid, followed by stirring at 0-70° C. for 3 to 8 h; e) separating the organic solvent and the acidic aqueous phase followed by washing the aqueous phase with an organic solvent; f) adjusting the pH in the aqueous phase by the addition of a base; and g) extracting the product into the organic phase followed by separation of the organic phase; and optionally h) treating the organic phase with a metal scavenger or charcoal to yield a (2S)-(4E)-N-methyl-5-[3-(5-alkoxypyridin)yl]-4-penten-2-amine.