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A kind of preparation method of tetrahydropyrrole compounds substituted by n-sulfonyl group

A technology for tetrahydropyrrole compounds, which is applied in the field of preparation of tetrahydropyrrole compounds, can solve the problems of cumbersome operation steps, limited scope of application, and limited applicability, and achieve high yield, easy source of raw materials, and convenient operation Effect

Inactive Publication Date: 2015-08-05
嘉兴南洋万事兴化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many defects in the above preparation method: as the required raw material butanediol sulfonate compound must be prepared in advance, the scope of application is not wide, the limitations are large, the operation steps are cumbersome, and the conditions are harsh, thus limiting its applicability

Method used

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  • A kind of preparation method of tetrahydropyrrole compounds substituted by n-sulfonyl group
  • A kind of preparation method of tetrahydropyrrole compounds substituted by n-sulfonyl group
  • A kind of preparation method of tetrahydropyrrole compounds substituted by n-sulfonyl group

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Experimental program
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Effect test

Embodiment 1

[0019] Example 1: N-p-toluenesulfonyl tetrahydropyrrole (I-1)

[0020] Mix 343.7mg (2mmol) p-toluenesulfonamide (Ⅲ-1) with 276.9mg (3mmol) 1,4-butanediol, in 3ml toluene, under the action of 68μl (0.4mmol) trifluoromethanesulfonic anhydride, Stir the reaction at 120°C and track the reaction by TLC. After 50 hours of reaction, the reaction solution is distilled to remove the solvent, and then column chromatography (the eluent is a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 5:1), followed by TLC. The eluate with an Rf value of 0.3-0.35 was collected, distilled under reduced pressure, and dried to obtain the target compound (I-1) with a yield of 96.2%.

[0021] 1H NMR (500MHz, CDCl3): δ1.76-1.73(m, 4H), 2.43(s, 3H), 3.14-3.21(m, 4H), 7.32(d, 2H, J=8.5Hz), 7.71(d ,2H,J=8.5Hz).

[0022]

Embodiment 2

[0024] The amount of trifluoromethanesulfonic anhydride was reduced to 34 μl (0.2 mmol), other operations were the same as in Example 1, and the yield was 78.8%.

Embodiment 3

[0026] The reaction temperature was changed to 90°C, other operations were the same as in Example 1, and the yield was 59.7%.

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Abstract

The invention discloses a preparation method of an N-sulfonyl substituted tetrahydropyrrole compound shown in formula (I), which comprises the following steps: adding a sulfamide compound shown in formula (III) and a 1,4-butanediol compound shown in formula (II) into an organic solvent; under the action of an acid catalyst, reacting the obtained mixture at a temperature of 30-200 DEG C; and after the reaction is completed through TLC (thin-layer chromatography) tracking detection, carrying out post-treatment on the reaction liquid so as to obtain the N-sulfonyl substituted tetrahydropyrrole compound shown in formula (I). The method disclosed by the invention is mild in reaction conditions, easy in raw material sources, low in cost, convenient to operate and high in yield; and through taking protonic anhydride as a catalyst, the method is green and environment-friendly.

Description

(1) Technical field [0001] The invention relates to a synthesis method of an intermediate, in particular to a preparation method of an N-sulfonyl substituted tetrahydropyrrole compound. (2) Background technology [0002] Tetrahydropyrrole compounds are important chemical raw materials and organic synthesis intermediates, widely used in medicine, pesticides and other fields. Among them, the synthesis method of N-sulfonyl substituted tetrahydropyrrole compounds has been rarely reported so far, and it is mainly prepared by the condensation reaction of butanediol sulfonate compounds and sulfonamides ((1) Eur.J.Org.Chem. , 2002, 2927-2931; (2) Tetrahedron Letters 2009, 50, 3237-3240). However, there are still many defects in the above preparation method: for example, the required raw material butanediol sulfonate compound must be prepared in advance, the scope of application is not wide, the limitations are relatively large, the operation steps are cumbersome, and the conditions...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/26C07D207/48
Inventor 崔冬梅石巍戚兰君张辰
Owner 嘉兴南洋万事兴化工有限公司