新产品编号:17911
Chemical Name: 2-[4-(1-Pyrrolidinyl)-2-butynyl]isoxazolidin-3-one
CAS No. 116445-17-1
项目整合开发状态: Preclinical
项目研究机构: Universit?degli Studi di Milano (Originator), Universit?degli Studi di Parma (Originator)
合成路线:In an alternative procedure,nucleophilic displacement of the nitro group from 3-nitro-2-isoxazoline (VI) with lithium benzylate gave the benzyl ether (VII),which was converted to isoxazolidinone (VIII) by catalytic hydrogenation.Alkylation of (VIII) with 1,4-dichloro-2-butyne (IX) resulted in a 4:1 mixture of regioisomers (X) and (XI).After chromatographic isolation,the desired isomer (X) was condensed with pyrrolidine (V) to provide the title compound.
📌 参考资料/链接：
参考文献标题:Synthesis and functional characterization of novel derivatives related to oxotremorine and oxotremorine-M
文献作者:Dallanoce,C.; Conti,P.; De Amici,M.; De Micheli,C.; Barocelli,E.; Chiavarini,M.; Ballabeni,V.; Bertoni,S.; Impicciatore,M.
参考来源:Bioorg Med Chem 1999,7(8),1539
📄 详细内容
合成路线:In an alternative procedure,nucleophilic displacement of the nitro group from 3-nitro-2-isoxazoline (VI) with lithium benzylate gave the benzyl ether (VII),which was converted to isoxazolidinone (VIII) by catalytic hydrogenation.Alkylation of (VIII) with 1,4-dichloro-2-butyne (IX) resulted in a 4:1 mixture of regioisomers (X) and (XI).After chromatographic isolation,the desired isomer (X) was condensed with pyrrolidine (V) to provide the title compound.
参考文献标题:Synthesis and binding affinity of new muscarinic ligands structurally related to oxotremorine
文献作者:Conti,P.; et al.
参考来源:Bioorg Med Chem Lett 1997,7(8),1033
合成路线:Alkylation of hydroxylamine with propargyl bromide (I) provided N-propargyl hydroxylamine (II),which was subsequently acylated with 3-chloropropionyl chloride (III) in the presence of pyridine to yield the N-hydroxy amide (IV).Mannich reaction of the propargyl compound (IV) with paraformaldehyde and pyrrolidine (V) with simultaneous cyclization of the N-hydroxy chloropropionamide furnished the title compound.
参考文献标题:Position 5 at the oxotremorinic skeleton as the stearing position for activity at the muscarinic receptors
文献作者:Amstutz,R.; et al.
参考来源:Helv Chim Acta 1987,702232