79199-62-5

Usage

Uses

Used in Pharmaceutical Industry:
(2S-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester is used as a key intermediate in the preparation of Argatroban (A769000), a direct thrombin inhibitor. Argatroban is utilized for the treatment of thrombotic disorders, particularly in patients with heparin-induced thrombocytopenia (HIT), where the use of heparin is contraindicated. (2S-cis)-4-Methyl-2-piperidinecarboxylic Acid Ethyl Ester plays a crucial role in the synthesis of this life-saving medication, contributing to its therapeutic efficacy and safety profile.

Upstream product

• 134984-62-6 ethyl cis-(2S,4R)-1-<(R)-1-phenylethyl>-4-methylpipecolate 
• 66937-93-7 4(R)-Methylpiperidine-2(R)-carboxylic acid ethyl ester 
• 78-79-5 isoprene 
• 134984-61-5 (6S)-1-<(R)-1-phenylethyl>-6-ethoxycarbonyl-4-methyl-3,4-didehydropiperidine 

Relevant academic research and scientific papers

Method for splitting isomer impurity of agathiban starting material

The invention provides a method for splitting the isomer impurity of an argatroban starting material. The method comprises the following steps: performing salt formation by taking 4-methyl-2-piperidinecarboxylate racemate as a raw material and taking D-(+

Enantio- and Diastereo-selective Synthesis of Pipecolic Acid Derivatives using the Aza-Diels-Alder Reaction of Imines with Dienes

Optically active pipecolic acid derivatives can be prepared by the aza-Diels-Alder reaction of simple dienes with the imine derived from ethyl glyoxylate and chiral 1-phenylethylamine; the cycloadditions are regiospecific, highly diastereoselective within the heterocyclic ring (>92percent exo with cyclic dienes, and 100percent endo with acyclic dienes), and lead to high asymmetric induction in most cases (average d.e. = 72percent).

Asymmetric Synthesis of Pipecolic Acid Derivatives Using the Aza-Diels-Alder Reaction

Imines of the type R-N=CHCO2Et can be coerced into undergoing a (4+2) cycloaddition with substituted dienes if the reaction is carried out in DMF in the presence of both water and acid; these reactions show extremely high regio- and diastereoselectivity.U