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3-3'-substituted 2,2'-dipyrrolidine compounds and salts thereof

A technology of bipyrrolidine and compound, applied in the field of compound, 2, can solve the problems of unsatisfactory results of catalytic activity or stereoselectivity, and achieve the effect of high catalytic activity and stereoselectivity

Inactive Publication Date: 2009-06-10
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few examples of using chiral diamines as catalysts in asymmetric catalytic reactions, and satisfactory results have not been obtained in terms of catalytic activity or stereoselectivity.

Method used

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  • 3-3'-substituted 2,2'-dipyrrolidine compounds and salts thereof
  • 3-3'-substituted 2,2'-dipyrrolidine compounds and salts thereof
  • 3-3'-substituted 2,2'-dipyrrolidine compounds and salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] R 1 , R 2 is α-methylbenzyl, R 3 , R 4 Be benzyloxy, the stereochemistry of each chiral carbon is the same as compound Ia, and the synthetic route is as follows:

[0022]

[0023] (1) Synthetic Compound IVa from Compound IIIa

[0024] Sodium hydride (1.4g, 60%, 35.0mmol) was suspended in dry N,N-dimethylformyl (15mL), and compound IIIa (4.5g, 12mmol) was dissolved in dry N,N-dimethylformyl Formamide (10mL), slowly added dropwise to the above sodium hydride suspension in N,N-dimethylformamide under ice bath, stirred for half an hour under ice bath, then benzyl bromide (1.6mL, 35.0mmol) was slowly added under ice bath, after the dropwise addition was completed, the resulting solution was stirred at room temperature for 4 hours, after the reaction was completed, water was added under ice bath, extracted with ether, the ether layer was dried with anhydrous sodium sulfate, filtered , after concentration, the obtained crude product was purified by column chromatograph...

Embodiment 2

[0029] R 1 , R 2 for Boc, R 3 , R 4 is OH, and the stereochemistry of each chiral carbon is the same as that of compound Ia:

[0030] Compound VIa (2.7g, 4.8mmol), palladium hydroxide / carbon (1.0g), (Boc) 2 O (3.1g, 14.4mmol) was dissolved in methanol and reacted for 24 hours under a hydrogen atmosphere (20atm). The reaction solution was filtered, concentrated, and purified by column chromatography to obtain the target compound (1.8g, 96%). 1 H NMR (400MHz, CDCl 3 )δ 4.19 (br, 2H), 3.42 (br, 6H), 2.30 (br, 2H), 2.18 (br, 2H), 1.87 (br, 2H), 1.42 (s, 18H).

Embodiment 3

[0032] R 1 , R 2 for Boc, R 3 , R 4 is OBn, the stereochemistry of each chiral carbon is the same as compound Ia:

[0033] Sodium hydride (60%, 48mg, 1.2mmol) was suspended in dry DMF (4mL), and the DMF (1.5mL) solution of the target compound (0.15g, 0.40mmol) in Example 3 was added under ice-cooling, and stirred for half After 1 hour, add benzyl bromide (140 μL, 1.2 mmol), stir at room temperature, add water (15 mL) after the reaction is complete, extract with ether (20 mL×3), combine organic layers, dry over anhydrous sodium sulfate, filter, concentrate and pass through the column layer The target compound (196 mg, 89%) was purified by analysis and purification, 1 H NMR (400MHz, CDCl 3 )δ7.2~37.36(m,10H), 4.31~4.48(m,4H), 3.36~3.54(m,4H), 3.64~3.76(m,4H), 1.97~2.32(m,4H), 1.44( s, 18H).

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Abstract

The invention relates to a 3,3' substituted 2,2'pyrrolidine compound and a salt thereof in the technical field of chemistry industry. The general formula of the compound is shown on the right, in which R1and R2 are hydrogen, alkyl groups having 1 to 18 carbon atoms, or acyl groups having 1 to 18 carbon atoms, R3 and R4 are hydrogen, alkyl groups having 1 to 18 carbon atoms, or OR<Z>, wherein R<Z> is hydrogen, an alkyl group having 1 to 18 carbon atoms, or an acyl group having 1 to 18 carbon atoms; R5 and R6 are hydrogen or alkyl groups having 1 to 18 carbon atoms, n equals to 1 or 2, X<-> is an anion, the chiral feature of the carbon labeled with * is R or S. The compounds belong to chiral diamine compounds, chiral diamine compounds and the salts thereof can be used as a chiral small-molecular catalyzer or a chiral ligand and applied to a plurality of unsymmetrical catalytic reactions, and have high catalytic activity and stereo selectivity.

Description

technical field [0001] The invention relates to a compound in the technical field of chemical industry, in particular to a 3,3'-substituted 2,2'-bipyrrolidine compound and a salt thereof. Background technique [0002] The preparation technology of chiral compounds is the core technology leading the fine chemical industry in the 21st century. Asymmetric catalytic technology is one of the most effective methods for preparing chiral compounds. The key to asymmetric catalysis technology lies in chiral catalysts, so the development of highly efficient chiral ligands and chiral catalysts has always been the focus of academic and industrial circles. Chiral diamines have the advantages of good stability and easy preparation, so chiral diamine ligands and chiral diamine catalysts are widely used in asymmetric catalytic reactions. For example, the hydrogenation catalyst containing chiral diamine developed by Noyori, the epoxidation and hydrolysis catalyst developed by Jacobsen, and ...

Claims

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Application Information

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IPC IPC(8): C07D207/04C07B53/00
Inventor 张勇健马元辉金尚彬张万斌
Owner SHANGHAI JIAO TONG UNIV
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