128013-69-4

Usage

Uses

Used in Pharmaceutical Industry:
3-(Aminomethyl)-5-methylhexanoic acid is used as an anticonvulsant for the treatment of seizures and epilepsy. Its GABA-mimetic properties help in modulating neuronal excitability, providing a calming effect on the central nervous system and reducing the frequency and severity of seizures.
Used in Controlled Substances:
In the United States, 3-(Aminomethyl)-5-methylhexanoic acid is classified as a controlled substance, which means its production, distribution, and use are regulated by the government. This classification is due to its potential for abuse and dependence, as well as its therapeutic applications in the treatment of certain medical conditions.
Used in Research and Development:
3-(Aminomethyl)-5-methylhexanoic acid is also utilized in research and development for the discovery of new drugs and therapies. Its GABA-mimetic properties make it a valuable tool in studying the role of GABA in the central nervous system and its potential applications in treating various neurological disorders.

InChI:InChI=1/C8H17NO2.H2O/c1-6(2)3-7(5-9)4-8(10)11;/h6-7H,3-5,9H2,1-2H3,(H,10,11);1H2

Upstream product

• 181289-15-6 (±)?3?(carbamoylmethyl)?5?methylhexanoic acid 
• 181289-17-8 (R,S)-3-cyano-5-methylhexanoic acid ethyl ester 
• 181289-33-8 (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid 
• 916982-10-0 3-isobutylglutarimide 
• 1198320-89-6 methyl 4-isobutyl-2-oxopyrrolidine-3-carboxylate 
• 1058692-72-0 2,2-dimethyl-5-[3'-methyl-1'-(nitromethyl)butyl]-1,3-dioxane-4,6-dione 
• 93498-13-6 2,2-dimethyl-5-(3'-methylbutylidene)-1,3-dioxane-4,6-dione 
• 100401-40-9 methyl 2-carbomethoxy-4-nitro-3-(2-methylpropyl)butyrate 
• 350801-68-2 3-cyano-5-methyl-hex-3-enoic acid ethyl ester 
• 1126426-26-3 4-isobutyl-2-oxo-pyrrolidin-3-carboxylic acid ethyl ester 
• 1126426-25-2 5-methyl-(2-ethylcarboxy)-3-nitromethylhexanoic acid ethyl ester 

Downstream Products

• 148553-50-8 pregabilin 
• 1026095-29-3 C₈H₈O₃*C₈H₁₇NO₂ 
• 1136478-30-2 3-(aminomethyl)-5-methylhex-5-enoic acid 
• 216576-74-8 3-(aminomethyl)-5-methylhex-4-enoic acid 
• 61312-87-6 4-(2-methylpropyl)pyrrolidin-2-one 
• 1166837-39-3 C₈H₁₇NO₂*C₁₃H₁₅NO₅ 
• 1165869-58-8 C₈H₁₇NO₂*C₁₁H₁₃NO₆S 
• 1165869-53-3 C₈H₁₇NO₂*C₁₂H₁₃NO₅ 
• 1165869-61-3 C₈H₁₇NO₂*C₁₂H₁₅NO₆S 
• 1136499-07-4 (S)-(+)-3-aminomethyl-5-methylhexanoic acid di-(O,O')-p-toluoyl-D-tartaric acid salt 
• 1136499-06-3 (R)-(-)-3-aminomethyl-5-methylhexanoic acid (-)-(O,O')-di-p-toluoyl-D-tartaric acid salt 
• 185815-62-7 (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid (S)-mandelate 
• 1078737-39-9 (S)-pregabalin-(-)-O,O'-dibenzoyl-L-tartrate 

Relevant academic research and scientific papers

A ring-closing metathesis approach for the synthesis of (±)-pregabalin

Efficient utilization of a Mannich-type reaction and the ring-closing metathesis (RCM) approach that leads to a convenient synthesis of 3-(aminomethyl)-5-methylhexanoic acid (pregabalin) is described. Springer-Verlag 2011.

General synthesis of 3-substituted alkenyl GABA as potential anticonvulsants

Stereospecific synthesis of cis and trans 3-substituted vinyl-γ- aminobutyric acid analogs were obtained by either a Claisen rearrangement or a Witrig reaction from common diene precursors.

Synthesis of (±)-Pregabalin by Utilizing a Three-Step Sequential-Flow System with Heterogeneous Catalysts

(±)-Pregabalin, a γ-amino acid derivative, has been synthesized by utilizing flow methods. A three-step sequential-flow reaction starting from commercial isovaleraldehyde and methyl malonate proceeded smoothly with heterogeneous catalysts to afford the precursor of pregabalin in yields of 75–100 %, and a space-time yield of 52.2 g/L d was reached. In addition, a heterogeneous catalyst for the Knoevenagel reactions of aldehydes with malonates, which is the first step of the synthesis, has been developed. Pregabalin was finally obtained by acid-catalyzed hydrolysis of the precursor followed by neutralization.

PROCESS FOR THE PREPARATION OF GAMMA AMINO BUTYRIC ACIDS AND ANALOGS THEREOF

The present invention relates to a process for the preparation of gamma aminobutyric acid derivatives of formula I, in particular pregabalin, baclofen and analogs thereof. Further, this process is comprised of preparation protocol for compounds of formula I, involving Michael addition and Beckmann rearrangement strategy.

Method for preparing pregabalin by photocatalysis (by machine translation)

The preparation method is characterized by comprising the 3S following -3 - steps:5 - 1) dissolving the compound I and a certain amount of alkali in an organic solvent, adding the compound II, heating the reaction, obtaining the compound III, 2) preparing the compound V; 3) preparing the compound V through deprotection, ring opening, chiral resolution, and recrystallization to obtain pregabalin. The preparation method comprises the following steps: 1) dissolving compound III, compound IV and photocatalyst in an organic solvent. The raw materials used in the invention are cheap and easily available, the reaction conditions of the photocatalytic oxidation method are mild, reagents are environmentally friendly, green and environment-friendly, and the method is an ideal industrial production process. (by machine translation)

Method for preparing 3-aminomethyl-5-methylcaproic acid

The invention relates to a method for preparing 3-aminomethyl-5-methylcaproic acid, belonging to the technical field of chemistry. According to the preparation method, 3-methyl formate-5-methylhexanoic acid is used as a raw material, and the target product 3-aminomethyl-5-methylcaproic acid can be prepared through two steps of reactions including ammonia ester exchange and reduction. The method has the beneficial effects of simple process route, high product purity of 99.0% or above, less three wastes, no toxic agent, mild reaction conditions and low cost, and is suitable for industrial production.

Preparation method of pregabalin

The invention discloses a preparation method of pregabalin, and particularly discloses a synthesis method of pregabalin, and relates to a compound shown as a formula I shown in the specification.

Method for preparing 4-isobutyl pyrrolidone by solvent-free method

The invention discloses a method for preparing 4-isobutyl pyrrolidone by a solvent-free method. The method is characterized in that R-type, S-type or racemic 3-(carbamylmethyl)-5-methylhexanoic acid is used as an initial raw material, 3-aminomethyl-5-methylhexanoic acid is prepared through a Hofmann degradation reaction, and an R-type, S-type or racemic 4-isobutyl pyrrolidone product is prepared through a solvent-free reaction. According to the method, currently prepared sodium hypobromite is used for carrying out the Huffman degradation reaction, so that the defects that sodium hypochlorite is easy to decompose and low in reaction activity can be avoided. The generated 3-aminomethyl-5-methylhexanoic acid is subjected to a melting reaction under the solvent-free condition, pulping and purification are carried out, a small amount of oxidation impurities can be removed, meanwhile, the solid form is improved, finally, suction filtration and drying are carried out, and the 4-isobutyl pyrrolidone product with the purity being 98.5% or above is obtained. In the whole reaction process, less solvent is used, the operation is simple and easy, and the method is clean and environment-friendly.

Synthesis of (+/-)-Pregabalin and its novel lipophilic β-alkyl-substituted analogues from fatty chains

In this work, were synthesized for the first time a series of new lipophilic β-alkyl substituted GABA derivatives from fatty alkyl chains. The synthesis of these GABA analogues was investigated by two different bicomponent approaches as a key step. The results showed low yields in the path from aliphatic nitroolefins and Meldrum's acid, whereas the Knoevenagel condensation between aliphatic aldehydes and Meldrum's acid afforded fatty alkylidenes in good yields (75-97%). These compounds were subsequently subjected to a conjugate addition reaction with nitromethane, resulting in the fatty Michael adducts (in 87-97% yields) which were in turn submitted to a one pot domino hydrolysis-decarboxylation, leading to the isolation of β-alkyl-substituted γ-nitro acids in good yields (78-92%). Finally, the reduction of the fatty γ-nitro acids allowed for the access to new lipophilic β-alkyl substituted GABA analogues, which were isolated in high yields (90-98%). The new methodology was also applied to the synthesis of antiepileptic drug (+/-)-Pregabalin, which was obtained after four steps in high overall yield. This journal is

Method for preparing pregabalin racemate

The invention belongs to the technical field of organic chemistry, and in particular relates to a method for preparing a pregabalin racemate. The method comprises the following steps: uniformly mixing3-carbamoymethyl-5-methylhexanoic acid and NaOBr, conducting heating with a water bath of 40 to 45 DEG C to enable the system to undergo a process of being automatically heated to 81-85 DEG C due toreaction heat release, and then automatically lowering the temperature to 50-60 DEG C for 1 hour; and heating the reaction system to 80 DEG C for 2 hours. The above automatic temperature raising process facilitates Hoffman rearrangement, thereby increasing the reaction conversion rate and the yield of the pregabalin racemate. The preparation method of the invention is high in yield, good in reproducibility and easy for industrial production.