GW-320659, 1555U88, BW-1555U88
Chemical Name: (2S,3S,5R)-2-(3,5-Difluorophenyl)-3,5-dimethylmorpholin-2-ol hydrochloride
CAS No. 135306-42-2, 135414-64-1 (racemic, (2alpha,3alpha, 5alpha)-isomer)
项目整合开发状态: Phase II
项目研究机构: GlaxoSmithKline (Originator)
合成路线:3,5-Difluorobenzonitrile (I) was treated with ethylmagnesium bromide to give propiophenone (II),which was subsequently brominated with dioxane dibromide yielding bromoketone (III).Condensation of (III) with (R)-2-amino-1-propanol (IV) in the presence of 2,6-lutidine produced the corresponding amino ketone,which spontaneously cyclized to the title cyclic hemiacetal form.
📌 参考资料/链接：
参考文献标题:Novel morpholinol cpds.,their preparation and use
文献作者:Kelley,J.L.; Musso,D.L.; Boswell,G.E.; Cooper,B.R.(GlaxoSmithKline plc)
参考来源:AU 9165639; EP 0426416; JP 1991206084; US 5104870
📄 详细内容
合成路线:3,5-Difluorobenzonitrile (I) was treated with ethylmagnesium bromide to give propiophenone (II),which was subsequently brominated with dioxane dibromide yielding bromoketone (III).Condensation of (III) with (R)-2-amino-1-propanol (IV) in the presence of 2,6-lutidine produced the corresponding amino ketone,which spontaneously cyclized to the title cyclic hemiacetal form.
参考文献标题:(2S,3S,5R)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol: A novel antidepressant agent and selective inhibitor of norepinephrine uptake
文献作者:Kelley,J.L.; Musso,D.L.; Boswell,G.E.; Soroko,F.E.; Cooper,B.R.
参考来源:J Med Chem 1996,39(2),347