148553-51-9

Basic information

• Product Name: Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-
• Synonyms: Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-;(R)-3-(AMinoMethyl)-5-Methylhexanoic acid;ent-Pregabalin;PD 144550;Pregabalin IMpurity V;Pregabalin R-Isomer;Pregabalin Related Compound A Minimum Pack;EOS-60963
• CAS NO: 148553-51-9
• Molecular Formula: C₈H₁₇NO₂
• Molecular Weight: 159
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 148553-51-9.mol

Chemical Properties

• Boiling Point: 274 °C at 760 mmHg
• Flash Point: 119.5 °C
• Appearance: /
• Density: 0.997 g/cm³
• PKA: 4.23±0.10(Predicted)
• CAS DataBase Reference: Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-(148553-51-9)
• EPA Substance Registry System: Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-(148553-51-9)

Safety Data

• Hazardous Substances Data: 148553-51-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3R)is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
In the chemical industry, Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3R)can be used as a building block for the synthesis of more complex molecules. Its versatile structure makes it a valuable starting material for creating a wide range of chemical products.
Used in Research and Development:
Due to its unique structure and properties, Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3R)is also used in research and development for studying various chemical reactions and exploring new applications in different fields.
Used in Chiral Compounds:
The (3R)configuration of this compound makes it a valuable chiral compound, which can be used in the study of stereochemistry and the development of enantiomerically pure drugs with improved efficacy and reduced side effects.

Upstream product

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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 
• 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 
• 61312-87-6 4-(2-methylpropyl)pyrrolidin-2-one 

Relevant articles and documents

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 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.

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 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.

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 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.

Organic photocatalysis for the radical couplings of boronic acid derivatives in batch and flow

We report an acridium-based organic photocatalyst as an efficient replacement for iridium-based photocatalysts to oxidise boronic acid derivatives by a single electron process. Furthermore, we applied the developed catalytic system to the synthesis of four active pharmaceutical ingredients (APIs). A straightforward scale up approach using continuous flow photoreactors is also reported affording gram an hour throughput.

Preparation method of antiepileptic drug-pregabalin

The invention discloses a preparation method of an antiepileptic drug-pregabalin, belonging to the field of drug synthesis. According to the preparation method, a compound 2 is taken as a raw material, and the pregabalin is prepared by the synthesis steps of enabling the raw material and a Grignard reagent to be subjected to an addition reaction, carrying out deprotection, ring-opening and chiralresolution, and the like. Compared with the methods reported in the existing literatures, the preparation method provided by the invention avoids the use of heavy metal reagents, and is fewer in synthesis steps, higher in process stability, simple to operate and mild in reaction conditions, thus being suitable for large-scale production.

Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation

An intermolecular 1,2-carboamination of unactivated alkenes proceeding via a Pd(II)/Pd(IV) catalytic cycle has been developed. To realize this transformation, a cleavable bidentate directing group is used to control the regioselectivity of aminopalladation and stabilize the resulting organopalladium(II) intermediate, such that oxidative addition to a carbon electrophile outcompetes potential β-hydride elimination. Under the optimized reaction conditions, a broad range of nitrogen nucleophiles and carbon electrophiles are compatible coupling partners in this reaction, affording moderate to high yields. The products of this reaction can be easily converted to free ?3-amino acids and ?3-lactams, both of which are common structural motifs found in drug molecules and bioactive compounds. Reaction kinetics and DFT calculations shed light on the mechanism of the reaction and explain empirically observed reactivity trends.