128013-65-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Methyl-3-nitromethyl-hexanoic Acid, Ethyl Ester is used as a synthetic intermediate for the production of Pregabalin, a widely prescribed medication for various conditions such as epilepsy, neuropathic pain, and generalized anxiety disorder. Its role in the synthesis process is crucial for the development of this effective therapeutic agent.
Used in Chemical Synthesis:
As a synthetic intermediate, 5-Methyl-3-nitromethyl-hexanoic Acid, Ethyl Ester is also used in the development of other chemical compounds and materials. Its unique structure and properties make it a versatile building block for creating new molecules with potential applications in various industries.
Chemical Properties:
5-Methyl-3-nitromethyl-hexanoic Acid, Ethyl Ester is a colorless liquid, which indicates its stability and suitability for use in various chemical reactions and processes. Its physical state and properties contribute to its utility as a synthetic intermediate in the pharmaceutical and chemical industries.

InChI:InChI=1/C10H19NO4/c1-4-15-10(12)6-9(5-8(2)3)7-11(13)14/h8-9H,4-7H2,1-3H3

Upstream product

• 75-52-5 nitromethane 
• 34993-63-0 5-methyl-2-hexenoic acid ethyl ester 
• 1071-46-1 hydrogen ethyl malonate 
• 590-86-3 isovaleraldehyde 
• 1166864-51-2 (+/-) ethyl 5-methyl-3-bromo-hexanoate 
• 34993-63-0 ethyl (E)-5-methylhex-2-enoate 

Downstream Products

• 148553-50-8 pregabilin 
• 61312-87-6 4-(2-methylpropyl)pyrrolidin-2-one 
• 128013-69-4 (R,S)-3-iso-butyl-4-aminobutyric acid 

Relevant academic research and scientific papers

Synthesis method of pregabalin intermediate 3-nitromethylene-5-methyl-ethyl hexanoate

The invention provides a synthesis method of a pregabalin intermediate, namely 3-nitromethylene-5-methyl-ethyl hexanoate. The synthesis method comprises the following steps: (1) reacting isovaleraldehyde with malonic acid in a choline chloride-urea eutectic solvent to obtain 5-methyl-2-hexenoic acid; (2) reacting the 5-methyl-2-hexenoic acid with absolute ethyl alcohol in a choline chloride-methanesulfonic acid eutectic solvent to obtain 5-methyl-2- ethyl hexanoate; and (3) reacting the 5-methyl-2- ethyl hexanoate with nitromethane in a choline chloride-urea eutectic solvent to obtain the 3-nitromethylene-5-methyl- ethyl hexanoate. The method does not need an organic solvent, is green, low in toxicity, environment-friendly, simple to operate, simple in post-treatment, high in yield and lowin cost, and is a green and efficient synthesis method for synthesizing the pregabalin intermediate.

Preparation method of pregabalin intermediate ethyl 3-nitromethyl-5-methylhexanoate

The invention discloses a preparation method of a pregabalin intermediate ethyl 3-nitromethyl-5-methylhexanoate. The method comprises the steps: reacting raw materials, namely ethyl 5-methyl-2-hexenoate as shown in a formula I and nitromethane in an appropriate organic solvent A at 20-150 DEG C under the action of a supported organic catalyst by taking nitromethane as a nucleophilic reagent to prepare ethyl 3-nitromethyl-5-methylhexanoate as shown in a formula II, wherein the organic solvent A is one selected from the followings: acetonitrile, methanol, ethyl acetate, dichloromethane, ethanol,toluene and 1,4-dioxane. Ethyl 3-nitromethyl-5-methylhexanoate is prepared by using the supported organic catalyst low in cost, easy to prepare and environment-friendly and is high in reaction yieldand product purity.

PROCESS FOR PREPARING PREGABALIN

The invention relates to a process for preparing a compound of formula (I): wherein said process comprises hydrogenation of a compound of formula (II); under alkaline conditions, wherein R represents hydrogen or a labile group capable of being converted to hydrogen. The invention also relates to intermediates used in said process, to the use of said intermediates in the preparation of pregabalin and to a process for resolving racemic compounds of formula (I).

PROCESS FOR PREPARING PREGABALIN

The invention relates to a process for preparing a compound of formula (I): wherein said process comprises hydrogenation of a compound of formula (II): under alkaline conditions, wherein R represents hydrogen or a labile group capable of being converted to hydrogen. The invention also relates to intermediates used in said process, to the use of said intermediates in the preparation of pregabalin and to a process for resolving racemic compounds of formula (I).

PROCESS TO PREGABALIN

The present invention relates to a novel method for the preparation of racemic pregabalin (1) or a single enantiomer thereof, (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid (2).

Intermediates for the preparation of Pregabalin and process for their preparation

The present invention relates to intermediates useful for the preparation of Pregabalin and to a process for their preparation.

PROCESSES TO PREGABALIN

The present invention relates to a novel method for the preparation of racemic pregabalin (1) or a single enantiomer thereof, (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid (2).

A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main compounds of interest involved are given, together with their CD spectra.