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

Description

Brivaracetam (alfaR, 4S)-Isomer is a racetam derivative with anticonvulsant properties. It is a 4-n-propyl analog of levetiracetam and is used as an impurity in the preparation of Brivaracetam (B677645), which is a medication primarily used for the treatment of epilepsy.

Uses

Used in Pharmaceutical Industry:
Brivaracetam (alfaR, 4S)-Isomer is used as a reagent for the preparation of 2-Oxo-1-pyrrolidine derivatives, which possess anticonvulsant activity. This application is significant in the development of new medications for the treatment of epilepsy and other seizure disorders.
Additionally, as an impurity of Brivaracetam (B677645), the alfaR, 4S)-Isomer plays a role in the production process of this anticonvulsant medication, contributing to its overall effectiveness in managing epilepsy.

Upstream product

• 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 (2S)-2-(4-propylpyrrolidin-2-one)butanamide 
• 357337-00-9 ((2R)-2-[(4R)-2-oxo-4-propyltetrahydro-1H-pyrrol-1-yl]butanamide) 
• 357336-99-3 C₁₁H₂₀N₂O₂ 
• 941290-08-0 1-((S)-1-carbamoyl-propyl)-2-oxo-5-propylpyrrolidine-3-carboxylic acid methyl ester 
• 2163-48-6 diethyl propylmalonate 
• 112106-16-8 (R)-2-((tert-butoxycarbonyl)methyl)pentanoic acid 
• 63095-51-2 (+)-(R)-4-propyl-4,5-dihydrofuran-2(3H)-one 

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.

Preparation methods of brivaracetam and intermediate thereof

The invention discloses a preparation method of a brivaracetam intermediate as shown in a formula B-R. The preparation method comprises the following steps: reacting a compound as shown in a formula B-P with a resolution reagent to prepare a compound as shown in a formula B-Q; and converting the compound as shown in the formula B-Q into the brivaracetam intermediate as shown in the formula B-R. The resolution reagent is a (1S, 2S)-(+)-1, 2-cyclohexanediamine compound. The invention also provides a preparation method of brivaracetam. According to the methods, a mixture of two diastereoisomers of (S)-2-3-propylpyrrolidine-1-yl butyric acid can be conveniently and effectively split, a chiral chromatographic column is not used, the process time is greatly shortened, the operation is simplified, the process cost is reduced, and industrial production and environmental protection are facilitated.

PROCESS FOR THE PREPARATION OF BRIVARACETAM

The present invention relates to a process for the preparation of brivaracetam, a compound of formula I and salts thereof. The present invention also relates to a compound of formula II and a compound of formula IIA, process for its preparation and conversion thereof to brivaracetam, the compound of formula I.