683206-53-3Relevant academic research and scientific papers
An efficient enantiopure synthesis of a pivotal precursor to substance P antagonists
Nugent, Thomas C.,Seemayer, Robert
, p. 142 - 148 (2012/12/21)
Many substance P antagonists have a core structure based on the quinuclidine skeleton. Manufacture of these drug antagonists proceeds through the advanced intermediate (2S,3S)-cis-2-benzhydryl-3-aminoquinuclidine 1, and all previous syntheses of 2S,3S-1 p
PROCESS FOR THE PREPARATION OF (S,S)-CIS-2-BENZHYDRYL-3-BENZYLAMINOQUINUCLIDINE
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Page 10-11, (2008/06/13)
A process for preparing (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine. The process includes the steps of contacting a compound containing a mixture of R- and S-isomers and having Formula (I), with an effective amount of a chiral organic acid in the presence of an organic solvent and an effective amount of an organic carboxylic acid for converting the R-isomer into an acid salt of the S isomer, wherein the organic solvent is capable of solubilizing the compound containing the mixture of R- and S-isomers, while precipitating the acid salt and the organic carboxylic acid is different from the chiral organic acid; neutralizing the acid salt with a base to provide an S-isomer of a chiral ketone of Formula (II), and reacting the chiral ketone with an organic amine in the presence of a Lewis acid to provide the corresponding imine and reducing the imine.
