357336-99-3

Basic information

• Product Name: Brivaracetam (alfaR, 4S)-Isomer
• Synonyms: Brivaracetam (alfaR, 4S)-Isomer;2R-2-[(4S)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
• CAS NO: 357336-99-3
• Molecular Formula: C11H20N2O2
• Molecular Weight: 212.29
• Mol File: 357336-99-3.mol
• Article Data: 56

Chemical Properties

• Boiling Point: 409.3±28.0 °C(Predicted)
• Appearance: /
• Density: 1.062±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 15.74±0.50(Predicted)
• CAS DataBase Reference: Brivaracetam (alfaR, 4S)-Isomer(CAS DataBase Reference)
• NIST Chemistry Reference: Brivaracetam (alfaR, 4S)-Isomer(357336-99-3)
• EPA Substance Registry System: Brivaracetam (alfaR, 4S)-Isomer(357336-99-3)

Safety Data

• Hazardous Substances Data: 357336-99-3(Hazardous Substances Data)

Usage

Uses

αR,4S-Brivaracetam acts as a reagent for the preparation of 2-Oxo-1-pyrrolidine derivatives and their anticonvulsants activity. Also an impurity of Brivaracetam (B677645), a 4-n-propyl analog of levetiracetam (L331500), and a racetam derivative with anticonvulsant properties.

Upstream product

• 110-62-3 pentanal 
• 357338-13-7 (2S)-4,5-dehydro-(2-oxo-4-n-propyl-1-pyrrolidinyl)-2-butanamide 
• 7324-11-0 (S)-2-amino-butanamide 
• 78920-10-2 5-hydroxy-4-n-propyl-2,5-dihydrofuran-2-one 
• 664305-06-0 3-(iodomethyl)hexanoic acid 
• 357336-99-3 C₁₁H₂₀N₂O₂ 
• 145032-58-2 ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 

Downstream Products

• 357336-99-3 ((2S)-2-[(4S)-2-oxo-4-propyltetrahydro-1H-pyrrol-1-yl]butanamide) 
• 357337-00-9 ((2R)-2-[(4R)-2-oxo-4-propyltetrahydro-1H-pyrrol-1-yl]butanamide) 
• 357336-99-3 ((2R)-2-[(4S)-2-oxo-4-propyltetrahydro-1H-pyrrol-1-yl]butanamide) 
• 357336-20-0 brivaracetam 
• 357336-99-3 C₁₁H₂₀N₂O₂ 

Relevant articles and documents

Chiral resolution method of brivaracetam

The invention relates to a chiral resolution method of brivaracetam. The chiral resolution method comprises the following steps: 1) in a solvent, co-crystallizing a compound (R,S)-2-((R)-2-oxo-4-propyl pyrrolidin-1-yl)butyramide as shown in a formula 2 and D-tartaric acid to obtain a compound as shown in a formula 3; 2) performing alkali dissociation on the compound as shown in the formula 3 to obtain a compound as shown in a formula 1; and 3) carrying out epimerization on the other diastereoisomer compound as shown in the formula 4 in the step 1) under the action of alkali to obtain a compound as shown in the formula 2, and continuously preparing the compound as shown in the formula 1. According to the method, brivaracetam and diastereoisomers can be separated easily and conveniently, so high-purity brivaracetam is prepared.

Intermediate for synthesizing brivaracetam and preparation method thereof

The invention provides an intermediate compound for synthesizing brivaracetam, namely (2S)-2-(5-oxy-3-propyl-2, 5-dihydrofuran-2-yl) amino) butylamide (I), and a preparation method of the intermediatecompound. The compound (I) comprises (S)-2(((R)-5-oxy-3-propyl-2, 5-dihydrofuran-2-yl) amino) butyramide (I)-R, or (S)-2-(((S)-5-oxy-3-propyl-2, 5-dihydrofuran-2-yl) amino) butyramide (I)-S, or a mixture of (I)-R and (I)-S in any proportion. The compound shown in the formula (I) can be used for synthesizing brivaracetam, and a novel method is provided for designing a concise and efficient brivaracetam synthesis route.

Novel preparation method of iracetam

The preparation method comprises the following steps: (R)-4 -propyl dihydrogen -2 (3H) - ketone which is purchased in the market as a raw material under a certain condition, and three-step synthesis of iracetam. To the preparation method provided by the invention, a chiral preparative chromatographic column separation step is not needed, and high optical purity Biracetam can be obtained directly. The method is high in yield. Post-treatment is simple and convenient, low in production cost, is fit for industrial production.