36489-13-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(Aminomethyl)cyclopropanecarboxylic acid is utilized as a building block in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the creation of diverse molecules with potential therapeutic applications.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, 2-(Aminomethyl)cyclopropanecarboxylic acid is studied for its potential pharmacological properties. It has been investigated for its role as an inhibitor of certain enzymes, which could contribute to the development of new drugs targeting specific biological pathways.
Used in Organic Chemistry:
2-(Aminomethyl)cyclopropanecarboxylic acid is also employed in organic chemistry for the synthesis of various organic compounds. Its cyclopropane ring and aminomethyl group provide a versatile platform for the formation of new chemical entities with potential applications in different industries.

InChI:InChI=1/C5H9NO2/c6-2-3-1-4(3)5(7)8/h3-4H,1-2,6H2,(H,7,8)/t3-,4+/m0/s1

Upstream product

• 7688-51-9 N,N-bis(trimethylsilyl)allylamine 
• 6832-16-2 methyl diazoacetate 
• 213757-85-8 (1S,2R)-2-(Acetylamino-methyl)-cyclopropanecarboxylic acid 
• 169532-12-1 (1R,5S)-3-aza-2-oxobicyclo<3.1.0>hexane 
• 213757-87-0 (1S,2S)-2-(Acetylamino-methyl)-cyclopropanecarboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 213757-85-8 (1R,2R)-2-(Acetylamino-methyl)-cyclopropanecarboxylic acid 
• 213757-82-5 (1R,2S)-2-(Acetylamino-methyl)-cyclopropanecarboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 213757-83-6 (1S,2R)-2-(Acetylamino-methyl)-cyclopropanecarboxylic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 496810-98-1 (1R,2S)-2-Azidomethyl-cyclopropanecarboxylic acid methyl ester 
• 496810-97-0 (1R,2S)-2-Bromomethyl-cyclopropanecarboxylic acid methyl ester 
• 89395-28-8 (1R,5S)-3-oxabicyclo[3.1.0]hexan-2-one 
• 88335-87-9 (1S,RS)-cis-2-methoxycarbonyl-cyclopropane-1-carboxylic acid 
• 826-34-6 dimethyl cis-cyclopropane-1,2-dicarboxylate 
• 496811-01-9 (1R,2S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

A novel stereoselective tin-free radical protocol for the enantioselective synthesis of pyrrolidinones and its application to the synthesis of?biologically active GABA-derivatives

Optically pure 4-alkyl-pyrrolin-2-ones were synthesized from chiral N-allyl-α-bromoacetamides in high selective and stereo-controlled fashion, via a sequential 5-exo-trig radical cyclization-hydrogen or bromine atom-transfer process, under non-tin conditi

Application of polymer-supported enzymes and reagents in the synthesis of γ-aminobutyric acid (GABA) analogues

Polymer-supported pig liver esterase was used for the resolution of meso-diesters. The enzyme can be recovered quantitatively from the reaction mixture by filtration and reused without significant loss of activity. Further transformation of the resulting enantiomerically enriched carboxylic acids through the application of polymer-supported reagents and scavengers provides a number of GABA-analogues.

Resolution and conformational analysis of diastereoisomeric esters of cis- and trans-2-(aminomethyl)-1-carboxycyclopropanes

(1R,2S)-, (1S,2R)-, (1R,2R)- and (1S,2S)-2-(Aminomethyl)-1- carboxycyclopropanes, conformationally restricted analogues of the neurotransmitter γ-aminobutyric acid (GABA), have been resolved by chromatographic separation of the corresponding diastereoisomeric esters which were formed between the cis- and trans-2-(acetamidomethyl)1- carboxycyclopropanes with (R)-(-)-pantolactone. 1H NMR, semi-empirical conformational analysis, ab initio (DFT) structure and NMR shielding tensor calculations of the cis-diastereoisomers allowed the absolute configuration assignments of the cis-amino acids.

An Efficient Route to GABA-Analogous Amino Acids: Cyclopropanation of N-Silylated Allylamines and Enamines

N-Silylated allylamines 1 are effectively transformed into methyl cyclopropanecarboxylates 2 by methyl diazoacetate under Rh2(OAc)4 catalysis.Derivatives 2a and 2b are smoothly converted into trans-substituted amino acids 6a and 6b, respectively, and to bicyclic γ-lactams 5a and 5b.The pharmacologically interesting γ-aminobutyric acid (GABA) analogue trans-6a is now available in few steps.Photochemical and thermal Fe(CO)5-induced hydrogen shift converts allylamine derivatives 1 into N-silylated enamines 7.While enamine (E)-7a can be cyclopropanated with methyl diazoacetate under Cu(acac)2 catalysis to afford the desired cyclopropane derivatives 8a in good yield, the other enamines are rather unreactive towards the carbenoid.Use of an optically active catalyst provides 8a with an ee of 56percent (cis) and 20percent (trans).Acid induced ring cleavage of 8a gives the β-formyl ester 10a, and reduction of 8a followed by desilylation provides the aminocyclopropane 14 in good overall yield, thus demonstrating that cyclopropanes like 8a can serve as useful synthetic intermediates. --- Key Words: Amino acids / GABA analogues / Aminocyclopropanes / Enamines, N-silylated / Cycloaddition

Synthesis of &γ-Aminobutyric Acid Analogue of Restricted Conformation. Part 1. The 2-(Aminomethyl)cycloalkaneacetic Acids

The synthesis of analogues with restricted rotatin about the C(2)-C(3) bond of γ-aminobutyric acid, namely cis- and trans-2-(aminomethyl)-cyclopropane and -cyclobutanecarboxylic acids and trans-2-(aminomethyl)cyclohexanecarboxylic acid are described.