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Method for preparing pregabalin intermediate

A compound and reaction technology, which is applied in the field of preparation of pregabalin intermediates, can solve problems such as long reaction time, cumbersome process, and unsafety, and achieve the effects of simple operation, high yield, and mild reaction conditions

Inactive Publication Date: 2017-11-28
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, patent application CN200910266661.8 or WO2006110783 discloses related methods for preparing 4-isobutyl-2-pyrrolidone; but these methods need to use hydrogen and / or high-pressure equipment or use other substrates to go through multiple steps to obtain, the reaction Long time, cumbersome process and / or large unsafe factors

Method used

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  • Method for preparing pregabalin intermediate
  • Method for preparing pregabalin intermediate
  • Method for preparing pregabalin intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Preparation of compound 3

[0020] Add 15g of pyrrolidine-2,4-dione and 26g of isobutyltriphenylphosphine bromide into 200ml of N,N-dimethylformamide, lower the temperature to 0°C, and add 17g of potassium tert-butoxide in batches, Warm up to room temperature, continue to stir for 5 hours, TLC spot plate to monitor the completion of the reaction, pour the reaction solution into 800ml of water, add ethyl acetate to extract three times, combine the organic phases, add anhydrous sodium sulfate to dry, filter, and concentrate under reduced pressure to obtain 16.8 g of crude compound 3 was directly used in the next reaction without further purification.

Embodiment 2

[0022] Preparation of 4-isobutyl-2-pyrrolidone

[0023] Add 16.8g of the crude product of compound 3 into 150ml of tetrahydrofuran, cool down to 0°C, slowly add 15.2g of sodium triacetoxyborohydride, stir at room temperature overnight, monitor the completion of the reaction by TLC spotting, add saturated ammonium chloride, and then add water Extract with ethyl acetate to obtain an organic phase, add anhydrous sodium sulfate, filter, concentrate under reduced pressure, and distill the obtained residue under reduced pressure to obtain 18.6 g of 4-isobutyl-2-pyrrolidone. The total yield is 87%, the purity is 99.51%, m / z=142[M+1].

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Abstract

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.

Description

Technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a preparation method of pregabalin intermediate. Background technique [0002] Pregabalin has analgesic, anticonvulsant and anxiolytic activities and has a preventive effect on epileptic seizures. 4-Isobutyl-2-pyrrolidone (1) is a key intermediate in the synthesis of pregabalin. Easily obtaining qualified 4-isobutyl-2-pyrrolidone (02) is of great significance to the synthesis of pregabalin. [0003] [0004] There are various methods for preparing 4-isobutyl-2-pyrrolidone in the prior art. For example, patent applications CN200910266661.8 or WO2006110783 disclose related methods for preparing 4-isobutyl-2-pyrrolidone; however, these methods require the use of hydrogen and / or high-pressure equipment or other substrates to go through multiple steps to obtain the reaction. It takes a long time, the process is cumbersome and / or there are major unsafe factors. There...

Claims

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Application Information

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IPC IPC(8): C07D207/267
CPCC07D207/267
Inventor 不公告发明人
Owner 湖南华腾制药有限公司
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