1690-74-0

Usage

Uses

Used in Pharmaceutical Industry:
1-methyl-piperidine-2-carboxylic acid methyl ester is used as a key building block for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be incorporated into the development of new drugs, enhancing their therapeutic properties and effectiveness in treating a range of medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 1-methyl-piperidine-2-carboxylic acid methyl ester serves as an intermediate in the production of various agrochemicals. Its ability to be integrated into the synthesis of pesticides and other agricultural chemicals contributes to the development of more effective and targeted solutions for crop protection and pest management.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 1-methyl-piperidine-2-carboxylic acid methyl ester is utilized for the preparation of a wide range of organic compounds. Its reactivity and functional groups make it a valuable component in the synthesis of complex organic molecules, including those with potential applications in various industries such as materials science, fragrances, and dyes.
Safety Precautions:
Due to its potentially hazardous nature, 1-methyl-piperidine-2-carboxylic acid methyl ester should be handled and stored with appropriate safety measures. This includes the use of personal protective equipment, proper ventilation, and adherence to established safety guidelines to minimize the risk of exposure and ensure the well-being of those working with this chemical compound.

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 124685-63-8 pentacarbonyl(N-methyl-2-azacyclohexylidene)chromium⁽⁰⁾ 
• 2459-07-6 methyl pyridine-2-carboxylate 
• 39160-67-3 1-methyl-2-methoxycarbonylpyridinium iodide 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1057585-91-7 2-[3-(5-bromo-2,3-dimethoxyphenyl)-[1,2,4]oxadiazol-5-yl]-1-methylpiperidine 
• 18747-95-0 1-methyl-2-piperidinecarbonitrile 
• 20845-34-5 (1-methyl-piperidin-2-yl)-methanol 

Relevant academic research and scientific papers

1,4-Dihydropicolinic acid derivatives: Novel NADH analogues with an altered connectivity pattern

Sodium dithionite reduction of α-substituted N-alkylpyridinium salts (derived from picolinic acid derivatives) afforded the corresponding 1,4-dihydropyridines with a new substitution pattern, in which the electron-withdrawing group is at the α-position. These compounds promote biomimetic reductions and are hence considered functional NADH analogues.

Alkylation of 2-Lithio-N-Methylpiperidines and -pyrrolidines: Scope, Limitations, and Stereochemistry

The scope and limitations of the alkylation of racemic and nonracemic 2-lithipiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported.These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield.With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating.With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases.Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products.A mechanistic interpretation is presented.

Photolytic reactions of chromium aminocarbene complexes. Conversion of amides to α-amino acids

A variety of tertiary amides was converted to chromium aminocarbene complexes by reaction with Na2Cr(CO)5 and trimethylsilyl chloride. Photolysis of these carbene complexes in methanol or tert-butyl alcohol solvent produced α-amino esters in good to excellent yield. Aminocarbene complexes containing chiral oxazolidine groups were synthesized and photolyzed in alcohol to produce chiral α-amino esters in 50-93% de. Pentacarbonyl[(dibenzylamino)(methyl)carbene]chromium(0) was prepared in high yield by the N-benzylation of the corresponding monobenzyl amino complex. Base-assisted alkylation of the methyl group with a variety of halides followed by photolysis in methanol produced the alkylated alanine methyl ester in excellent overall yield. Other aminocarbene complexes underwent similar reactions. With chiral, optically active aminocarbene complexes, the alkylated alanine derivative was produced with high diastereoselectivity.

REGIOSPECIFIC FUNCTIONALISATION OF CARBON ATOMS α TO HETEROCYCLIC NITROGEN

Previously, methods have been devised to functionalise the two endocyclic C atoms α to the piperidine N.In the present study we show that a nitrile substituent can be introduced also to the exocyclic α-C, making the centre either nucleo- or electrophilic in subsequent transformations.NMR studies have been used to gain knowledge of the mechanistic aspects leading to the observed regiospecificity.The generality of the method, along with the ease of operation, high yields and regiospecificity, make it highly versatile for synthetic purposes.