61312-87-6

Basic information

• Product Name: 4-Isobutyl-2-pyrrolidinone
• Synonyms: 2-pyrrolidinone, 4-(2-methylpropyl)-;4-isobutylpyrrolidin-2-one;4-isobutyl-2-pyrrolidinone(SALTDATA: FREE);4-Isobutyl-2-pyrrolidinone (pregabalin lactaM iMpurity);4-(2-Methylpropyl)-;Pregabalin IMpurity IV;Pregabalin LactaM IMpurity;4-ISOBUTYL-2-PYRROLIDIN-1-YLNE
• CAS NO: 61312-87-6
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21
• Product Categories: Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocyclic Compounds;Heterocycles
• Mol File: 61312-87-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 269.066°C at 760 mmHg
• Flash Point: 152.254°C
• Appearance: /
• Density: 0.928g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.445
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 16.66±0.40(Predicted)
• CAS DataBase Reference: 4-Isobutyl-2-pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isobutyl-2-pyrrolidinone(61312-87-6)
• EPA Substance Registry System: 4-Isobutyl-2-pyrrolidinone(61312-87-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 61312-87-6(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

Different sources of media describe the Uses of 61312-87-6 differently. You can refer to the following data:
1. Impurity in commercial preparation of Pregabalin.
2. Pregabalin intermediate
3. Pregabalin (P704800)

InChI:InChI=1/C8H15NO/c1-6(2)3-7-4-8(10)9-5-7/h6-7H,3-5H2,1-2H3,(H,9,10)

Upstream product

• 128013-65-0 3-nitromethyl-5-methyl-hexanoic acid ethyl ester 
• 148553-50-8 pregabilin 
• 181289-33-8 (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid 
• 53618-21-6 dimethyl 2-(3-methylbutylidene)malonate 
• 1198320-89-6 methyl 4-isobutyl-2-oxopyrrolidine-3-carboxylate 
• 24502-08-7 (E)-4-methylpent-2-enal 
• 128013-69-4 (R,S)-3-iso-butyl-4-aminobutyric acid 
• 1191278-90-6 Methyl 3-(dimethoxymethyl)-5-methylhexanoate 
• 1119-16-0 isocaproic aldehyde 
• 626-89-1 4-Methyl-1-pentanol 
• 100401-40-9 methyl 2-carbomethoxy-4-nitro-3-(2-methylpropyl)butyrate 
• 590-86-3 isovaleraldehyde 
• 121505-31-5 4-methyl-2-methylenepentan-1-ol 
• 87438-94-6 ethyl 2-isobutylacrylate 

Downstream Products

• 128013-69-4 (R,S)-3-iso-butyl-4-aminobutyric acid 
• 148553-50-8 pregabilin 
• 181289-22-5 (R)-(+)-4-isobutyl-2-pyrrolidinone 
• 181289-23-6 (S)-4-isobutyl-pyrrolidin-2-one 

Relevant articles and documents

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 intermediate

The invention discloses a method for preparing a pregabalin intermediate 4-isobutyl-2-pyrrolidone. The method comprises the following steps: by taking pyrrolidine-2,4-diketone as a raw material, carrying out a wittig reaction so as to obtain a compound 3, and carrying out a double-bond hydrogenation reaction on the compound 3 so as to obtain a compound 1, thereby obtaining the target product pregabalin intermediate 4-isobutyl-2-pyrrolidone. The method is simple in operation and high in yield and is a process suitable for large-scale industrial production.

STEREOSELECTIVE REDUCTIVE AMINATION OF ALPHA-CHIRAL ALDEHYDES USING OMEGA-TRANSAMINASES FOR THE SYNTHESIS OF PRECURSORS OF PREGABALIN AND BRIVARACETAM

The present invention relates to processes comprising a combined racemization and stereoselective reductive amination step in which an aldehyde compound of formula (I) is contacted with an (R)-selective ω-transaminase or an (S)-selective ω-transaminase to racemize the compound of formula (I) and obtain an amine compound of formula (II). These processes are useful for the preparation of precursors of pharmaceutically active agents such as brivaracetam and pregabalin.