25137-00-2

Basic information

• Product Name: (R)-(-)-Nipecotic acid
• Synonyms: (R)-(-)-NIPECOTIC ACID HCL;(R)-(-)-Nipecotic acid, (3R)-(-)-3-Carboxypiperidine;Ethyl (R)-nipecotate, 95+%;(R)-(-)-3-Piperidinecarboxylic acid;(R)-(-)-3-Piperidinecarboxylic acid 97%;(R)-(-)-3-PIPERIDINECARBOXYLIC ACID HYDROCHLORIDE;(R)-PIPERIDINE-3-CARBOXYLIC ACID HCL;(R)-(-)-PIPERIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE
• CAS NO: 25137-00-2
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• EINECS: 2017-001-1
• Product Categories: Nitrogen cyclic compounds;Beta amino acids;Piperidine;Piperidine Series;Chiral Reagent;Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 25137-00-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 251-255 °C
• Boiling Point: 265.8 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.02g/cm
• Vapor Pressure: 0.0026mmHg at 25°C
• Refractive Index: -4.5 ° (C=5, H2O)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Methanol (Very Slightly), Water (Sparingly)
• PKA: 3.88±0.20(Predicted)
• CAS DataBase Reference: (R)-(-)-Nipecotic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-Nipecotic acid(25137-00-2)
• EPA Substance Registry System: (R)-(-)-Nipecotic acid(25137-00-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: TM6125390
• Hazardous Substances Data: 25137-00-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

General Description

(R)-(-)-3-Piperidinecarboxylic acid is an inhibitor of GABA (γ-aminobutyric acid) uptake.

InChI:InChI=1/C6H11NO2/c8-6(9)5-2-1-3-7-4-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1

Upstream product

• 25137-01-3 (R)-ethyl nipecotate 
• 498-95-3 nipecotic acid 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 71962-74-8 Ethyl nipecotate 
• 4138-26-5 nipecotamide 
• 37675-18-6 (S)-(+)-nipecotic acid ethyl ester 
• 88466-74-4 (3S)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid 
• 2067-33-6 5-bromopentanoic acid 
• 1214903-21-5 3-piperidinecarboxamide dihydrochloride 
• 88495-54-9 (3S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid 
• 637337-43-0 (4R)-3-(5-bromo-1-oxopentyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 4509-90-4 5-bromovaleroyl chloride 
• 163438-09-3 (R)-1-Boc-nipecotic acid 
• 495-19-2 norarecoline 

Downstream Products

• 163438-09-3 (R)-1-Boc-nipecotic acid 
• 136059-25-1 (R)-N-(2-(3,3-Bis(4-Chlorophenyl)-2-propen-1-yloxy)-ethyl)-3-piperidinecarboxylic acid ethyl ester 
• 160706-62-7 (R)-1-((benzyloxy)carbonyl)piperidine-3-carboxylic acid 
• 88466-74-4 (3S)-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid 
• 1347758-06-8 (R)-1-(2-chloropyrimidin-4-yl)piperidine-3-carboxylic acid 
• 1347758-07-9 (R)-1-(2-chloropyrimidin-4-yl)-N-(4-methylbenzyl)-piperidine-3-carboxamide 
• 309748-80-9 (R)-tert-butyl 3-(phenylcarbamoyl)piperidine-1-carboxylate 
• 1536381-00-6 (3S)-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylic acid 
• 1536381-11-9 ammonium (3R)-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylate 
• 1537168-80-1 (3S)-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyrazin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylic acid 
• 1537168-83-4 (3R)-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyrazin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylic acid 

Relevant articles and documents

Discovery and Optimization of Imidazopyridine-Based Inhibitors of Diacylglycerol Acyltransferase 2 (DGAT2)

The medicinal chemistry and preclinical biology of imidazopyridine-based inhibitors of diacylglycerol acyltransferase 2 (DGAT2) is described. A screening hit 1 with low lipophilic efficiency (LipE) was optimized through two key structural modifications: (1) identification of the pyrrolidine amide group for a significant LipE improvement, and (2) insertion of a sp3-hybridized carbon center in the core of the molecule for simultaneous improvement of N-glucuronidation metabolic liability and off-target pharmacology. The preclinical candidate 9 (PF-06424439) demonstrated excellent ADMET properties and decreased circulating and hepatic lipids when orally administered to dyslipidemic rodent models.

Method for preparing (S)-3-piperidinecarboxylic acid

The invention discloses a method for preparing (S)-3-piperidinecarboxylic acid. The method includes steps of carrying out reaction on 3-piperidinecarboxamide or salt of the 3-piperidinecarboxamide in concentrated hydrochloric acid to obtain (S)-3-piperidinecarboxylic acid salt; converting the (S)-3-piperidinecarboxylic acid salt to obtain the (S)-3-piperidinecarboxylic acid. The method has the advantages that the reaction is carried out on the 3-piperidinecarboxamide or the salt of the 3-piperidinecarboxamide in the concentrated hydrochloric acid, accordingly, chiral resolution effects can be realized while hydrolysis is carried out, and resolution on the 3-piperidinecarboxamide or 3-piperidinecarboxylic acid by the aid of chiral resolving agents can be omitted; preparation processes are simple in post-treatment operation, N protection and de-protection processes are omitted, accordingly, the method is high in atomic economy and low in cost, and a simple, feasible and low-cost production method can be provided for synthesizing the (S)-3-piperidinecarboxylic acid.

PROCESS FOR PRODUCING SOLID AMINO ACID

The problem to be solved by the present invention is to ea lily and efficiently produce an amino acid having 2 to 7 carbon atoms as a high-purity solid without complicated operation, which is useful as a synthetic intermediate for medicines or agrochemicals. The present invention is characterized in comprising a step of precipitating solid amino acid with high purity. In the present invention, the by-produced salt composed of the sulfonic acid and the amine was removed to the mother liquor by reacting an amine with a sulfonic acid salt of amino acid in an aprotic polar solvent, or by reacting a sulfonic acid with an amine salt of amino acid in an aprotic polar solvent. The sulfonic acid salt of amino acid, for example, may be produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid, or by reacting an amino acid tert-butyl ester with a sulfonic acid.