An alternative route to the proline derivative (2S,5R)-5-ethoxycarbonylmethyl-pyrrolidine-2-carboxylic acid from protected glutamic acid

Marie-Priscille Brun (1) , Anne-Sophie Martin (2) , Christiane Garbay (3) , Laurent Bischoff (4)

1 PMC - UMR_S 648 - Pharmacochimie Moléculaire et Cellulaire
2 UPD5 Pharmacie - Université Paris Descartes - Faculté de Pharmacie de Paris
3 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques
4 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The synthesis of (2S,5R)-5-ethoxycarbonylmethyl-pyrrolidine-2-carboxylic acid was achieved in two steps, with an overall yield of 53%. This synthesis used Cbz-Glu-OBzl as the starting material and led to the titled compound with a d.e.>96%.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

Marie-Priscille Brun, Anne-Sophie Martin, Christiane Garbay, Laurent Bischoff. An alternative route to the proline derivative (2S,5R)-5-ethoxycarbonylmethyl-pyrrolidine-2-carboxylic acid from protected glutamic acid. Tetrahedron Letters, 2003, 44 (37), pp.7011-7013. ⟨10.1016/S0040-4039(03)01792-1⟩. ⟨hal-02385515⟩