1350815-39-2

Upstream product

• 139334-63-7 ethyl (2R)-4-methyl-1-((S)-1-phenylethyl)-1,2,3,6-tetrahydropyridine-2-carboxylate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 37662-06-9 ethyl <(S)-1-phenylethyl>iminoethanoate 
• 225377-18-4 1,1-dimethylethyl N-(2-ethoxy-2-oxoethyl)-N-<1(S)-phenylethyl>carbamate 
• 22263-68-9 ethyl 2-<<1(S)-phenylethyl>amino>acetate 

Downstream Products

• 79199-61-4 ethyl 4-methylpipeloate 

Relevant academic research and scientific papers

Diastereoselective approach to cis-4-methyl/thiol-pipecolic esters based on RCM reaction and conjugate michael addition

A synthetic route for the access to enantiopure cis-4-methyl/thiol- pipecolic esters is presented. It is based on the ring-closing metathesis reaction to build the β-unsaturated piperidin-2-one derived from (S)-(-)-phenylethylamine, followed by either diastereoselective conjugate addition of methylorganocuprate allowing access to cis-4-methyl pipecolic ester or by tandem diastereoselective hydrosulforization-thionization reaction providing access to cis-4-thiol pipecolic ethyl esters.

Diastereoselective synthesis of an argatroban intermediate, ethyl (2R,4R)-4-methylpipecolate, by means of a Mandyphos/rhodium complex-catalyzed hydrogenation

The synthetic antithrombotic argatroban is a dipeptide between the nonproteogenic (2R,4R)-4-methyl-2-piperidine carboxylic acid and l-arginine, in turn bonded to a methyltetrahydroquinoline sulfonyl group. An extensive screening of transition metal-based complexes with different ligands was performed in order to identify the best catalyst for the diastereoselective hydrogenation of a suitable 4,5-dehydropiperidine precursor aimed toward a synthesis of the (2R,4R)-4-methyl piperidine moiety. Copyright