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2,5-cis-bisubstituted pyrrolidine derivative and its preparing process and usage

A synthetic method, 5-cis-technology, applied in 2 fields, to achieve the effect of maintaining atom economy, easy availability of raw materials, and easy industrial production

Inactive Publication Date: 2003-01-15
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, a one-pot synthesis of polysubstituted pyrrolidine derivatives using transition metal-catalyzed multicomponent reactions starting from functionalized allenes has not been reported.

Method used

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  • 2,5-cis-bisubstituted pyrrolidine derivative and its preparing process and usage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1c

[0013] Example 1 cis-1-p-toluenesulfonyl-2-phenyl-3,3-dicarboxymethyl-5-(1'-styryl)pyrrolidine: Take a reaction tube and add 138 mg of carbonic acid under nitrogen protection Potassium, 15mg Pd(PPh 3 ) 4 , 78mg imine C 6 h 5 =N-Ts, add 2 mL of tetrahydrofuran solvent, then add 46 mg of dimethyl 2-(2',3'-alkenyl)malonate, and 61 mg of iodobenzene. React at 85°C for 6 hours, filter, and purify by column chromatography (n-hexane: ether = 5: 1) to obtain 111 mg of 1-p-toluenesulfonyl-2-phenyl-3,3-dicarboxylate-5-( 1'-Styryl)pyrrolidine (cis / trans>99:1), yield 86%. 1 H NMR (CDCl 3 , 300MHz): δ=7.53(d, J=8.29Hz, 2H), 7.30-7.41(m, 5H), 7.11-7.28(m, 7H), 5.86(s, 1H), 5.36(s, 1H), 5.25(s, 1H), 4.50(dd, J=11.68, 5.98Hz, 1H), 3.65(s, 3H), 3.15(s, 3H), 2.84(dd, J=13.70, 11.68Hz, 1H), 2.60 (dd, J=13.70, 5.98Hz, 1H), 2.39(s, 3H); MS (70eV): m / z (%): 520 (14.32) [M + +1], 364(100); IR(KBr): ν=1749, 1729, 1635, 1597, 1493, 1350, 1165cm -1 ;Elemental analysis: ...

Embodiment 2c

[0014] Example 2cis-1-p-toluenesulfonyl-2-phenyl-3-cyano-3-methylcarboxylate-5(1'-(4'-propylphenyl)-2'-propylpentene base) pyrrolidine: take a reaction tube, add 159mg sodium carbonate, 25mg Pd(PPh 3 ) 4 , 78mg imine C 6 h 5 =N-Ts, add 1,4-dioxane solvent 2mL, then add 59mg 2-(4'-propyl-2', 3'-pentadienyl) ethyl cyanoacetate, and 92mg p-propyl iodobenzene. Reacted at 85°C for 15 hours, filtered, and purified by column chromatography (n-hexane: ether = 5:1) to obtain 124 mg of 1-p-toluenesulfonyl-2-phenyl-3-cyano-3-methylcarboxylate-5 -(1'-(4'-propylphenyl)-2'-propylpentenyl)pyrrolidine (cis / trans>95:5), yield 81%. 1 HNMR (CDCl 3 , 300MHz): δ=7.23-7.75(m, 13H), 5.40(s, 1H), 4.39(dd, J=11.83, 5.70Hz, 1H), 3.67(s, 3H), 2.48-2.76(m, 4H ), 2.36(s, 3H), 2.26(t, J=6.97Hz, 4H), 1.56-1.70(m, 2H), 1.28-1.51(m, 4H), 0.86-0.99(m, 9H); MS( 70 eV): m / z (%): 612 (6.54) [M + ], 91(100); IR(KBr): ν=2262, 1773, 1742, 1640, 1355, 1168 cm -1 ;Elemental analysis: ...

Embodiment 3c

[0015] Example 3 cis-1-p-toluenesulfonyl-2-phenyl-3,3-dicarboxymethyl-5-(1'-(4"-methylstyryl)pyrrolidine: take a reaction tube, Add 138mg potassium carbonate, 15mg Pd(PPh 3 ) 4 , 194mg imine C 6 h 5 =N-Ts, add 2 mL of tetrahydrofuran solvent, then add 46 mg of dimethyl 2-(2',3'-alkenyl)malonate, and 66 mg of p-methyliodobenzene. React at 85°C for 12 hours, filter, and purify by column chromatography (n-hexane: ether = 5: 1) to obtain 122 mg of 1-p-toluenesulfonyl-2-phenyl-3,3-dicarboxylate-5-( 1'-(4'-methylstyryl)pyrrolidine (cis / trans>99:1), yield 92%. 1 H NMR (CDCl 3 , 300MHz): δ=7.46(d, J=8.40Hz, 2H), 7.25(d, J=8.40Hz, 2H), 7.04-7.22(m, 9H), 5.79(s, 1H), 5.24(s, 1H), 5.14(s, 1H), 4.41(dd, J=11.53, 5.86Hz, 1H), 3.57(s, 3H), 3.07(s, 3H), 2.76(dd, J=13.67, 11.53Hz, 1H ), 2.52 (dd, J=13.67, 5.86Hz, 1H), 2.32 (s, 3H), 2.31 (s, 3H); MS (70 eV): m / z (%): 533 (7.55) [M + ], 416(100); IR(KBr): ν=1771, 1746, 1646, 1597, 1511, 1350, 1162 cm -1 ;E...

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Abstract

The present invention relates to a 2.5-cis-substituted pyrrolidine derivative, its synthesizing process "Multi-component one reactor method" and its application in synthesizing molecular blocks of chiral adjuvant or ligand, or the compound containing bioactive pyrrolidinecycle.

Description

technical field [0001] The invention relates to a class of 2,5-cis-disubstituted pyrrolidine derivatives, a new synthesis method and use thereof. The method uses Pd(0) as a catalyst to catalyze the reaction of organic halides, 2-(2,3-alkenyl)-dimethyl malonate, and imines, and has high regioselectivity and high stereoselectivity in a one-pot method Synthesis of 2,5-cis-disubstituted pyrrolidine derivatives. As an important molecular cut-off, this compound itself may have certain physiological activities, and it can also be used to further synthesize some compounds containing pyrrolidine rings. These compounds containing pyrrolidine rings have strong biological activities, such as for α, β glucosidase, α, β mannosidase, galactosidase and other enzymes have inhibitory effect, have strong affinity for DNA, can be used as antibiotics, etc., and can also be used to further synthesize some chiral Adjuvants or Ligands. Background technique [0002] Since the pyrrolidine molecula...

Claims

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Application Information

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IPC IPC(8): C07D207/16
Inventor 麻生明焦宁
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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