288389-24-2Relevant academic research and scientific papers
Practical and large-scale synthesis of rac-(3S,4aR,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g] quinoline-3-carboxylic acid methyl Ester
B?nziger, Markus,Cercus, Jacques,Stampfer, Wolfgang,Sunay, Ustun
, p. 460 - 466 (2000)
3-Substituted octahydrobenzo[g]quinolines are important intermediates for pharmaceutically active compounds. A short, efficient synthesis, which is feasible for large-scale manufacturing of rac-(3S,4aR,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g] quinoline-3-carboxylic acid methyl ester is presented. As starting materials the cheap and readily available 1,6-dimethoxynaphthalene and ethoxymethylenecyanoacetic acid ethyl ester were chosen. All atoms of the skeleton were introduced in the first step, by the reaction of 7-lithiated 1,6-dimethoxynaphthalene with ethoxymethylenecyanoacetic acid ethyl ester. Subsequent hydrogenation, followed by Birch reduction and acidic cyclization gave the 6-methoxy-2,3,4,4a,5,-10-hexahydrobenzo[g]quinoline-3-carboxylic acid·hydrochloride in high yield. The trans fusion of the two six-membered rings was established after NaBH4 reduction. After esterification, n-propylation, and kinetic protonation of an intermittantly formed trimethylsilylketene acetal, the desired product was isolated in high yield and excellent purity.
Piperidine and piperazine derivatives as inhibitors of the abeta fibril formation
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, (2008/06/13)
The invention provides a compound of formula I wherein R, X, Y1 and Y2 are as defined in the description, and a process for preparing them. The compounds of formula I are useful as pharmaceuticals.
