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Method for preparing pyrrolidine derivative

A compound, selected technology, applied in the direction of organic chemistry, etc., can solve problems such as limited applicability, and achieve the effects of good functional group compatibility, high product yield, and simple process

Active Publication Date: 2013-07-24
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(Hofmann, A.W.Ber.Dtsch.Chem.Ges.1885, 18, 5. K.; Freytag, C.Ber.Dtsch.Chem.Ges.1909, 42, 3427.) But this method needs pre-functionalized amino to be amino halides, which greatly limits its applicability

Method used

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  • Method for preparing pyrrolidine derivative
  • Method for preparing pyrrolidine derivative
  • Method for preparing pyrrolidine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1, the preparation of compound 2a3-methyl-N-trifluoromethanesulfonyl tetrahydropyrrole

[0033]

[0034] Weigh 0.022g (0.10mmol) ammonia substrate trifluoromethanesulfonamide (1a) shown in formula II, 0.066g (0.20mmol) oxidant iodobenzene acetate, 0.019g (0.20mmol) alkali potassium acetate and 0.004g (0.40mmol) ligand acetylacetone and 0.017g (0.10mmol) catalyst silver acetate, mixed with 1.0mL solvent 1,2-chloroethane, injected into the system by syringe, heated to 120°C on Wattecs Reactor The intramolecular hydrogenation ring formation reaction was carried out with vigorous stirring for 12 hours. After the reaction was completed, the crude product was directly subjected to column chromatography (washing with 100mL sherwood oil, then washing with sherwood oil, dichloromethane, and a mixed solvent of ether (petroleum ether: dichloromethane: diethyl ether=60:6: 1, volume ratio) to obtain the target product 2a (yield 70%).

[0035] The structural confirmat...

Embodiment 2

[0041] Embodiment 2, the preparation of compound 2b

[0042]

[0043] Ammonia substrates, silver acetate, iodobenzene acetate, potassium acetate, acetylacetone, 1,2-dichloroethane.

[0044] Weigh 0.022g (0.10mmol) ammonia substrate trifluoromethanesulfonamide (1b) shown in formula II, 0.066g (0.20mmol) iodobenzene acetate, 0.019g (0.2mmol) potassium acetate and 0.004g in reaction tube (0.40mmol) acetylacetone and 0.017g (0.10mmol) silver acetate, mixed with 1.0mL 1,2-chloroethane, injected into the system from a syringe, heated to 120°C on a Wattecs Reactor and stirred vigorously for 2 hours, let After the reaction tube was cooled to room temperature, 0.066 g of iodobenzene acetate was added to the reaction tube, and then heated to 120 ° C on the Wattecs Reactor, and the reaction was vigorously stirred for 3 hours. After the reaction was completed, the crude product was directly subjected to column chromatography (first with 100 mL petroleum Rinse with ether, and then rinse ...

Embodiment 3

[0051] Embodiment 3, the preparation of compound 2c

[0052]

[0053] Ammonia substrates, silver acetate, iodobenzene acetate, potassium acetate, 1,2-dichloroethane.

[0054] Weigh 0.022g (0.10mmol) ammonia substrate trifluoromethanesulfonamide (1b) shown in formula II, 0.066g (0.20mmol) iodobenzene acetate, 0.019g (0.2mmol) potassium acetate and 0.004g in reaction tube (0.40mmol) acetylacetone and 0.017g (0.10mmol) silver acetate, mixed with 1.0mL 1,2-chloroethane, injected into the system from a syringe, heated to 120°C on a Wattecs Reactor and stirred vigorously for 2 hours, let After the reaction tube was cooled to room temperature, 0.066 g of iodobenzene acetate was added to the reaction tube, and then heated to 120 ° C on the Wattecs Reactor, and the reaction was vigorously stirred for 3 hours. After the reaction was completed, the crude product was directly subjected to column chromatography (first with 100 mL petroleum Rinse with ether, and then rinse with a mixed ...

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Abstract

The invention discloses a pyrrolidine derivative and a preparation method thereof. The structural general formula of the pyrrolidine derivative is as shown in formula I. The invention provides a high-efficient organic synthesis method for realizing direct intramolecular ammoniation reaction of a straight-chain amine compound with the help of a transition metal catalytic system. The method has the advantages of simple and convenient process, high product yield, mild reaction conditions, wide range of application of substrates and good compatibility of a functional group, realizes intramolecular ammoniation reaction taking amino alcohol and amine substrates as main bodies, and further has important application values.

Description

technical field [0001] The invention relates to a method for preparing tetrahydropyrrole derivatives. Background technique [0002] Tetrahydropyrrole derivatives widely exist in natural products and active drug molecules, and these compounds are also widely used in medicine, food, pesticides, daily chemicals, coatings, textiles, papermaking, photosensitive materials, polymer materials middle. At present, the synthesis of tetrahydropyrrole compounds mainly focuses on the catalyzed reaction of 1,4-butanediol with ammonia and tetrahydrofuran with ammonia. At the same time, pyrrole hydrogenation, pyrrolidone hydrogenation, etc. also provide a series of effective methods for synthesizing these compounds. However, such methods often require harsh reaction conditions. If the transition metal catalyst system can be used to realize the linear ammonia compound sp 3 The direct ammoniation reaction of carbon-hydrogen bonds will greatly reduce production costs, reduce energy consumpti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/48
Inventor 施章杰杨明瑜
Owner PEKING UNIV
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