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Preparation method of (S)-alpha-ethyl-2-keto-1-pyrrolidine acetamide

A technology of pyrrolidine acetamide and pyrrole acetonitrile, which is applied in the field of new antiepileptic drugs, can solve the problems of unfavorable industrial production, high price of starting raw materials, and injury to operators, and achieve great implementation value and social and economic benefits, low cost, Effects of Effective Recycling

Inactive Publication Date: 2005-08-10
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The disadvantages of the above process are: the price of the starting material is relatively expensive, the synthesis of the target compound needs six steps of reaction, the total yield of the reaction is low, and the use of highly toxic sodium cyanide or volatile and highly toxic hydrogen cyanide Acid, it is easy to cause injury to operators and cause environmental pollution
[0013] The disadvantages of the above process are: the cost of raw materials is relatively high, volatile raw materials and some corrosion-resistant reaction equipment need to be used in the operation, which is not conducive to the realization of industrial production

Method used

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  • Preparation method of (S)-alpha-ethyl-2-keto-1-pyrrolidine acetamide
  • Preparation method of (S)-alpha-ethyl-2-keto-1-pyrrolidine acetamide
  • Preparation method of (S)-alpha-ethyl-2-keto-1-pyrrolidine acetamide

Examples

Experimental program
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Embodiment 1

[0043] Embodiment 1: the synthesis of (S)-α-amino-butyrocyanine hydrochloride

[0044] At -40°C to -20°C, 3.96 g of trimethylsilyl azide cyanide (40 mmol) and catalyst SnCl 4 (40mmol) in dichloromethane (400mL) solution was slowly added dropwise 20mL containing N-(3,4,6-tripivaloyl-2-deoxyglucosyl) propyl imine (30mmol) dichloromethane solution ; The catalyst here can also be ZnCl 2 or TiCl 4 After the dropwise addition, under stirring, the solution was slowly heated to -20°C, and the reaction was carried out at -20°C and monitored by TLC. After the reaction was completed, the solvent was evaporated, and then the remaining residue was dissolved in 400ml CH 2 Cl 2, the organic layer was sequentially washed with 2N HCL (100ml), saturated NaHCO 3 (3 × 200ml) and water (200ml) washing, organic layer with MgSO 4 Drying, after drying, the solvent is evaporated, then hydrolyzed in a saturated hydrogen chloride isopropanol solution to obtain a solid precipitate, and recrystallize...

Embodiment 2

[0045] Embodiment 2: the synthesis of (S)-α-amino-butyrocyanine hydrochloride

[0046] At -20°C to 0°C, 3.96 g of trimethylsilylazide cyanide (40 mmol) and catalyst SnCl 4 (40mmol) in dichloromethane (400mL) solution was slowly added dropwise 20mL containing N-(3,4,6-tripivaloyl-2-deoxyglucosyl) propyl imine (30mmol) dichloromethane solution ; The catalyst here can also be ZnCl 2 or TiCl 4 After the dropwise addition, under stirring, the solution was slowly heated to 0°C, and the reaction was carried out at 0°C and monitored by TLC. After the reaction was completed, the solvent was evaporated, and then the remaining residue was dissolved in 400ml CH 2 Cl 2 , the organic layer was sequentially washed with 2N HCL (100ml), saturated NaHCO 3 (3 × 200ml) and water (200ml) washing, organic layer with MgSO 4 After drying, the solvent was evaporated after drying, and then hydrolyzed in a saturated hydrogen chloride isopropanol solution to obtain a solid precipitate, which was rec...

Embodiment 3

[0047] Embodiment 3: the synthesis of (S)-α-amino-butyrocyanine hydrochloride

[0048] SnCl 4 The amount was changed to (60 mmol) and the others were the same as in Example 1 to obtain 3.2 g (S)-α-amino-butyrocyanine hydrochloride (yield 90.4%).

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Abstract

A process for preparing (S)-alpha-ethyl-2-oxy-1-pyrrolidine acetamide includs providing N-(3,4,6-trineovaleryl-2-deoxyglucosyl) propylimine as chiral template, nucleophilic addition reaction to obtain N-(3,4,6-trineovaleryl-2-deoxyglucosyl)-alpha-aminobutylonitrile, hydrolyzing to obtain (S)-alpha-amino-butylonitrile, cyclizing to obtain (S)-alpha-ethyl-2-oxy-1-pyrrolacetonitrile, and sulforic acid hydrolyzing to obtain target product.

Description

(1) Technical field [0001] The invention relates to a preparation method of an important novel antiepileptic drug "levetiracetam", namely (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide. (2) Background technology [0002] In the prior art, the chemical synthesis methods of (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide include: [0003] 1. Prepare the target compound through ring closure reaction with (S)-α-aminobutyramide hydrochloride: [0004] [0005] And (S)-α-aminobutyramide hydrochloride then adopts propionaldehyde to obtain through multistep reaction as starting material: [0006] [0007] The disadvantages of the above process are: the price of the starting material is relatively expensive, the synthesis of the target compound needs six steps of reaction, the total yield of the reaction is low, and the use of highly toxic sodium cyanide or volatile and highly toxic hydrogen cyanide acid, it is easy to cause injury to operators and cause environmental pollution. [0008]...

Claims

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Application Information

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IPC IPC(8): C07D207/27
Inventor 章鹏飞周国斌
Owner HANGZHOU NORMAL UNIVERSITY
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