52346-11-9Relevant academic research and scientific papers
Piperidine and octahydropyrano[3,4-c] pyridine scaffolds for drug-like molecular libraries of the European Lead Factory
Narhe, Bharat D.,Breman, Arjen C.,Padwal, Jalindar,Vandenput, Dirk A.L.,Scheidt, Joeri M.,Benningshof, Jorg C.J.,van der Marel, Gijsbert A.,Overkleeft, Herman S.,van der Stelt, Mario,Filippov, Dmitri V.
, p. 5160 - 5170 (2017)
We report short and efficient scalable syntheses of enantiomerically pure (3R,4S)-3-(hydroxymethyl4-(hydroxyethyl))-piperidine and 1-hydroxymethyl-octahydro-1H-pyrano[3,4-c]pyridine scaffolds. The alkaloid core was readily synthesized from naturally occurring quinine and can serve as a valued starting point for drug-discovery. Cleavage of a terminal 1,2-diol and acid catalysed epoxide opening cyclization are the key steps involved. A number of members of a projected small-molecular library is synthesized for each scaffold.
VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE
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, (2013/11/19)
The present invention relates to the use of the vinyl quinuclidine enantiomer (R) of the following formula 2 as a synthesis intermediate in the preparation of (R)-mequitazine.
Asymmetric synthesis of (+)-mequitazine from quinine
Leroux, Sebastien,Larquetoux, Laurent,Nicolas, Marc,Doris, Eric
supporting information; experimental part, p. 3549 - 3551 (2011/09/14)
The first asymmetric synthesis of the antihistaminic drug mequitazine is reported. Our approach started from quinine, a Cinchona alkaloid, whose chiral information was exploited for setting up the stereogenic center of (+)-mequitazine.
