Lanperisone hydrochloride, NK-433
兰吡立松盐酸盐 兰吡立松 Chemical Name: (-)-2(R)-Methyl-3-(1-pyrrolidinyl)-1-[4-(trifluoromethyl)phenyl]propanone hydrochloride
CAS No. 116287-13-9, 116287-14-0 (free base)
项目整合开发状态: Phase III
项目研究机构: Nippon Kayaku (Originator)
合成路线:The Grignard reaction of 4-(trifluoromethyl)benzaldehyde (I) with ethylmagnesium bromide in ethyl ether gives 1-[4-(trifluoromethyl)phenyl]-1-propanol (II),which is oxidized with CrO3/H2SO4 yielding 4-(trifluoromethyl)propiophenone (III).The condensation of (III) with pyrrolidine (IV) and paraformaldehyde by means of HCl in refluxing isopropanol affords racemic 2-methyl-3-(1-pyrrolidinyl)propiophenone (V),which is finally submitted to optical resolution with N-acetyl-L-phenylglycine (VI) or D-malic acid (VII) and treated with dry HCl gas.
📌 参考资料/链接：
参考文献标题:An optically active propanone deriv.and process for producing the same and use thereof
文献作者:Shiozawa,A.; Ishikawa,M.; Sugimura,H.; Yamamoto,H.; Sakasai,T.; Ohtsuki,K.; Kurashige,S.(Nippon Kayaku Co.,Ltd.)
参考来源:EP 0266577; JP 1989131171
📄 详细内容
合成路线:The Grignard reaction of 4-(trifluoromethyl)benzaldehyde (I) with ethylmagnesium bromide in ethyl ether gives 1-[4-(trifluoromethyl)phenyl]-1-propanol (II),which is oxidized with CrO3/H2SO4 yielding 4-(trifluoromethyl)propiophenone (III).The condensation of (III) with pyrrolidine (IV) and paraformaldehyde by means of HCl in refluxing isopropanol affords racemic 2-methyl-3-(1-pyrrolidinyl)propiophenone (V),which is finally submitted to optical resolution with N-acetyl-L-phenylglycine (VI) or D-malic acid (VII) and treated with dry HCl gas.
参考文献标题:Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants
文献作者:Kurashige,S.; Izumi,G.; Shiozawa,A.; Narita,K.; Sakitama,K.; Ishikawa,M.
参考来源:Eur J Med Chem 1995,30(1),85-94
合成路线:The Grignard reaction of 4-(trifluoromethyl)benzaldehyde (I) with ethylmagnesium bromide in ethyl ether gives 1-[4-(trifluoromethyl)phenyl]-1-propanol (II),which is oxidized with CrO3/H2SO4 yielding 4-(trifluoromethyl)propiophenone (III).The condensation of (III) with pyrrolidine (IV) and paraformaldehyde by means of HCl in refluxing isopropanol affords racemic 2-methyl-3-(1-pyrrolidinyl)propiophenone (V),which is finally submitted to optical resolution with N-acetyl-L-phenylglycine (VI) or D-malic acid (VII) and treated with dry HCl gas.
参考文献标题:Lanperisone Hydrochloride
文献作者:Wroblewskki,T.; Castar,J.; Leeson,P.
参考来源:Drugs Fut 1998,23(5),485
产品链接: CAS No. 116287-13-9›› 产品链接: CAS No.116287-14-0››