Introduction of the Tryptamine and Tryptophan Side-Chains

摘要: A procedure developed by Specter and Anthony involves acylation oxalyl chloride followed reaction with an amine to give indol-3-ylglyoxamide. The glyoxamides are then reduced tryptamines. In the original LiAlH 4 was used, but alternative methods using diborane alane also successful. borane reductions generate amine-borane complexes, from which is liberated CsF or acidic hydrolysis. 5-Benzyloxygramine (28.0 g, 0.10 mol) ethyl nitromalonate (20.5 were dissolved in toluene (225 ml). solution heated at reflux a vigorous stream of nitrogen passing through solution. During heating, precipitation solid occurred, made stirring difficult, it disappeared on continued heating. until evolution dimethylamine complete (about h). cooled washed 2 N HCl (2 x 100 ml), 1 NaOH 100ml) water. dried (MgSO ) decolorized Magnesol. Ethyl 2-nitro-3-(5-benzyloxyindol-3-yl) propanoate (3.7 0.01 abs. ethanol (50 ml) hydrogenated over PtO catalyst (1.0 g) H uptake ceased 1.75 purged 20% aq. (4.0g) added.