134902-40-2

Basic information

• Product Name: 1,2-Piperidinedicarboxylic acid, 1-methyl ester
• Synonyms: 1,2-Piperidinedicarboxylic acid, 1-methyl ester;1-(methoxycarbonyl)-2-piperidinecarboxylic acid
• CAS NO: 134902-40-2
• Molecular Formula: C8H13NO4
• Molecular Weight: 187.19
• Mol File: 134902-40-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Piperidinedicarboxylic acid, 1-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Piperidinedicarboxylic acid, 1-methyl ester(134902-40-2)
• EPA Substance Registry System: 1,2-Piperidinedicarboxylic acid, 1-methyl ester(134902-40-2)

Safety Data

• Hazardous Substances Data: 134902-40-2(Hazardous Substances Data)

Usage

Chemical derivation

Derived from piperidine and carboxylic acid

Usage

Commonly used in organic synthesis and pharmaceutical research

Potential applications

Development of new drugs, building block for synthesis of various organic compounds

Role

Intermediate in the production of other chemicals

Occurrence

Found in research laboratories and chemical manufacturing facilities

Chemical structure

Unique

Reactivity

Versatile, making it valuable in chemistry and drug discovery.

Upstream product

• 182012-49-3 1,2-bis(methoxycarbonyl)piperidine 
• 79-22-1 methyl chloroformate 
• 4043-87-2 pipecolic Acid 

Downstream Products

• 133127-73-8 methyl 2-(2-propenyl)piperidinecarboxylate 

Relevant articles and documents

Efficient deracemization of pipecolic acid amides through enantioselective protonation of their lithium enolates: Insights into the origin of the transferred proton

A detailed study of the deracemization of pipecolic acid amides is reported. Enantioselective protonation of the lithium enolates of these amides with use of commercially available ephedrines led to enantiomeric excesses (ee values) higher than 99%. The success of the reaction was strongly dependent on the following parameters: the base, the reaction temperature, the structure of the chiral source, and the achiral quenching reagent. sBuLi and the bimetallic base "potassium alkoxide/nBuLi" were the only bases to allow complete formation of the enolate in conjunction with high stereocontrol of the protonation. Experiments with (+)- or (-)-ephedrine derivatives as chiral sources and deuteriated reagents gave evidence that both the OH and NH protons of ephedrine were involved in the stereoinduction. External delivery of the proton was mainly operative with the aniline derivative (+)-5, as shown by deuterium labeling experiments, whereas internal quenching was the major pathway observed with ephedrine (6). Finally, the deracemization procedure was successfully applied to prepare both enantiomers of N-protected pipecolic acid from racemic pipecolic acid (51 % overall yield, 99% ee).

Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M2 receptors

Enantiomers of 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidin-1-yl]ethylamino]-carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (AF-DX 384) 1, have been synthesized from (S)-(+) and (R)-(-)-2-[N,N-dipropylaminomethyl]piperidine 4. The enantiomeric excess of 1 has been determined by capillary electrophoresis by using the α-highly sulphated cyclodextrin (α-HSCD) as chiral selector within the running electrolyte. (S)-(+)-(4) was prepared from (S)-(-)-pipecolic acid in a 4-step procedure (overall yield: 30%, ee: 99%) and (R)-(-)-AF-DX 384 from (R)-(+)-pipecolic acid. The (R)-(-) isomer exhibited in vitro a 23-fold higher affinity than its enantiomer (S)-(+) towards muscarinic receptors of subtype 2. Copyright (C) 2000.