UCB-34714

布瓦西坦 布瓦西坦外消旋体 Chemical Name: 2(S)-[2-Oxo-4(R)-propylpyrrolidin-1-yl]butyramide; (alphaS,4R)-alpha-Ethyl-2-oxo-4-propyl-1-pyrrolidineacetamide
CAS No. 357336-20-0, 357335-87-6 (racemate)
项目整合开发状态: Phase II
项目研究机构: UCB (Originator)
合成路线:The condensation of 2-pyrrolidone (I) with 2-oxobutyric acid (II) in refluxing toluene gives 2-(2-oxopyrrolidin-1-yl)-2-butenoic acid (III),which is treated with PCl5 in THF to yield the acyl chloride (IV).The reaction of (IV) with dry ammonia affords the corresponding amide (V),which is finally submitted to an asymmetric hydrogenation with H2 over a chiral Rh catalyst to provide the desired chiral butyramide.

合成路线:Reductive amination of 5-hydroxy-4-propyl-2-furanone (I) with (S)-2-aminobutyramide (II) in the presence of NaBH4 yields the dihydropyrrolone (III).Transfer hydrogenation of (III) with ammonium formate and Pd/C provides a diastereoisomeric mixture of pyrrolidinones,from which the title compound is isolated by preparative HPLC on chiral phase.