83680-83-5

Basic information

• Product Name: L-Pipecolicacid
• Synonyms: S-2-Pipecolinic acid
• CAS NO: 83680-83-5
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.16
• Mol File: 83680-83-5.mol
• Article Data: 117

Chemical Properties

• Boiling Point: 265.8 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.125 g/cm³
• CAS DataBase Reference: L-Pipecolicacid(CAS DataBase Reference)
• NIST Chemistry Reference: L-Pipecolicacid(83680-83-5)
• EPA Substance Registry System: L-Pipecolicacid(83680-83-5)

Safety Data

• Hazardous Substances Data: 83680-83-5(Hazardous Substances Data)

Usage

General Description

L-Pipecolic acid is a naturally occurring organic compound and a derivative of the amino acid lysine. It is found in various plant and animal tissues and plays a role in the biosynthesis of the neurotransmitter gamma-aminobutyric acid (GABA). L-Pipecolic acid is also known for its potential therapeutic applications, such as in the treatment of metabolic disorders and neurological conditions. Additionally, it has been studied for its antioxidant and anti-inflammatory properties, as well as its ability to modulate immune function. L-Pipecolicacid has garnered interest in the fields of medicine, biochemistry, and nutrition due to its diverse biological activities and potential health benefits.

Upstream product

• 4043-87-2 pipecolic Acid 
• 31456-71-0 (2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid 
• 98-98-6 2-Picolinic acid 
• 156-86-5 L-homoarginine 
• 1190-49-4 N-6-(aminocarbonyl)-L-lysine 
• 2418-95-3 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 
• 1190-48-3 N^ε-formyl-(2S)-lysine 
• 56879-47-1 (2R,3R)-3-hydroxypiperidine-1-carboxylic acis 
• 19889-77-1 (RS)-piperidine-2-carboxamide 
• 15912-30-8 (2S)-2-piperidinecarboxylic acid L-tartrate 
• 147-71-7 D-tartaric acid 
• 87-69-4 L-Tartaric acid 
• 78348-46-6 N-benzoyl-2-piperidinecarboxylic acid 
• 158221-57-9 (4R,9aS)-4-Phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one 

Downstream Products

• 47285-65-4 (S)-1-(2-Benzyloxycarbonylamino-acetyl)-piperidine-2-carboxylic acid 
• 128120-99-0 (S)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(2-oxo-2-phenyl-ethyl) ester 
• 945833-49-8 [1,4']-bipiperidinyl-2,1'-dicarboxylic acid 1'-tert-butyl ester 
• 1374119-20-6 2-(3-((R)-3-(3,4-dimethoxyphenyl)-1-((S)-1-(2-((1S,2R)-2-ethyl-1-hydroxy-cyclohexyl)-2-oxoacetyl)piperidine-2-carbonyloxy)propyl)phenoxy)acetic acid 
• 1374119-21-7 2-(3-((R)-3-(3,4-dimethoxyphenyl)-1-((S)-1-(2-((1R,2S)-2-ethyl-1-hydroxycyclohexyl)-2-oxoacetyl)piperidine-2-carbonyloxy)propyl)phenoxy)acetic acid 
• 111555-81-8 (S)-1-acetylpiperidine-2-carboxylic acid 
• 856838-98-7 (2S)-1-butylpiperidine-2-carboxylic acid 
• 74408-01-8 (R)-1-(Toluene-4-sulfonyl)-piperidine-2-carboxylic acid ethyl ester 
• 15923-61-2 (R)-α,α-diphenyl-2-piperidine methanol 
• 1218651-70-7 (R)-1-isopropylpiperidine-2-carboxylic acid 

Relevant articles and documents

Preparation method of caine drug intermediate (S)-2-piperidinecarboxylic acid

The invention discloses a preparation method of a caine drug intermediate (S)-2-piperidinecarboxylic acid. The preparation method specifically comprises the following steps of a) carrying out a one-pot reaction on 5-chlorovaleraldehyde, L-phenylglycinol and trimethylsilyl cyanide under the action of a catalyst A to obtain a compound as shown in a formula (I), wherein the catalyst A is magnesium diiodide, magnesium dibromide and magnesium perchlorate, (b) carrying out catalytic hydrogenation reaction on the compound as shown in the formula (I) to obtain (S)-2-cyano piperidine as shown in a formula (II), and (c) hydrolyzing the compound as shown in the formula (II) to obtain (S)-2-piperidinecarboxylic acid as shown in a formula (III). The preparation method utilizes cheap and easily available organic raw materials, and has the advantages of simple operation, mild reaction conditions, good stereoselectivity, high yield and the like.

A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics

A novel and enantioselective synthesis of (S)-2-pipecolic acid (5) has been achieved from Oppolzer’s sultam (1) and ethyl N-(diphenylmethylene)glycinate (2) as readily available starting materials. The highly stereoselective alkylation of chiral glycine intermediate (3) with 1,4-dibromobutane afforded the key backbone of (S)-2-pipecolic acid (5) in one-step that was utilized into the preparation of the local anesthetics mepivacaine, ropivacaine and bupivacaine.

Preparation method of (S)-2-piperidinecarboxylic acid

A preparation method of (S)-2-piperidinecarboxylic acid comprises the following steps: under the catalysis of Lewis acid, carrying out condensation reaction on L-camphor sulfonamide (I) and diphenyl imine ester (II) to generate a compound (III); enabling the compound (III) and the compound (IV) to be subjected to asymmetric alkylation under the action of strong base, imine hydrolysis under an acidic condition and intramolecular cyclization by a one-pot method to obtain a compound (V); and removing a chiral auxiliary group from the compound (V) under an alkaline condition to obtain a target compound (S)-2-piperidinecarboxylic acid (TM), wherein the formulas (I), (II), (III), (IV) and (V) are described in the specification. The target product can be obtained through three steps in total, themethod has the advantages of cheap and easily available raw materials, short route, high yield, good stereoselectivity and the like, and the (S)-2-piperidinecarboxylic acid is an important chiral intermediate of multiple medicines at present and has a good market prospect.