Epoxy-fused 2-methylene pyrrolidine compound and preparation method thereof

A methylene pyrrolidine and compound technology, which is applied to the field of epoxy-fused 2-methylene pyrrolidine compounds and their preparation, can solve the problems of unobtainable raw materials, complicated post-processing process and the like, and achieve convenient post-processing. , simple and easy synthesis method, the effect of high reaction yield

Inactive Publication Date: 2021-03-16
ZHEJIANG UNIV CITY COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the embodiment of the present application is to provide an epoxy-fused 2-methylene pyrrolidine compound and a preparation metho

Method used

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  • Epoxy-fused 2-methylene pyrrolidine compound and preparation method thereof
  • Epoxy-fused 2-methylene pyrrolidine compound and preparation method thereof
  • Epoxy-fused 2-methylene pyrrolidine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0034] Example 1: (1R, 5S / 1S, 5R)-4-methylene-1-phenyl-3-toluenesulfonyl-6-oxa-3-azabicyclo[3.1.0]hexane

[0035]

[0036] 4-Methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide (0.5mmol, 1.0 equivalent), cesium carbonate (1.0mmol, 2.0 equivalent) and dimethyl (propane-2- Alkyn-1-yl)sulfonium bromide salt (1.0mmol, 2.0eq) was dissolved in 10mL of dichloromethane and stirred overnight at 0–10°C until the reaction of the raw materials was complete. After the reaction was completed, the reaction system was filtered, and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was separated and purified by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain a yellow oil with a yield of 86%.

[0037] Yellow oil, yield 86%. 1 H NMR(400MHz,DMSO)δ7.72(d,J=8.3Hz,2H),7.42(s,1H),7.40(s,1H),7.39-7.33(m,5H),5.20(s,1H) , 4.92 (s, 1H), 4.35 (d, J = 12.4Hz, 1H), 4.26 (s, 1H), 4.18 (d, J = 12.4Hz, 1H), 2.39 (s, 3H). 13 C NMR (100 MHz,...

Example Embodiment

[0051] Example 2: (1R, 5S / 1S, 5R)-4-methylene-1-phenyl-3-toluenesulfonyl-6-oxa-3-azabicyclo[3.1.0]hexane

[0052]4-Methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide (0.1mmol, 1.0 equivalent), cesium carbonate (0.15mmol, 1.5 equivalent) and dimethyl (propane-2- Alkyn-1-yl)sulfonium bromide salt (0.15mmol, 1.5eq) was dissolved in 1mL of acetonitrile and stirred overnight at 20°C until the reaction of the raw materials was complete. After the reaction was completed, the yield was calculated by HPLC analysis, and the yield was 45%. In addition to acetonitrile, the solvent can also be any one of toluene, 1,4-dioxane, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, and methanol.

Example Embodiment

[0053] Example 3: (1R, 5S / 1S, 5R)-4-methylene-1-phenyl-3-toluenesulfonyl-6-oxa-3-azabicyclo[3.1.0]hexane

[0054] 4-Methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide (0.1mmol, 1.0 equivalent), 1,8-diazabicycloundec-7-ene (0.15 mmol, 1.5 equivalents) and dimethyl (prop-2-yn-1-yl) sulfonium bromide salt (0.15 mmol, 1.5 equivalents) were dissolved in 1 mL of dichloromethane, stirred overnight at 20 ° C until the raw materials reacted complete. After the reaction was completed, the yield was calculated by HPLC analysis, and the yield was 47%. In addition to 1,8-diazabicycloundec-7-ene (DBU), the base may be selected from potassium carbonate, sodium carbonate, sodium hydroxide, sodium ethoxide, pyridine, N,N-diisopropyl Ethylamine (DIEA), Triethylamine, 4-Dimethylaminopyridine (DMAP).

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Abstract

The invention discloses an epoxy-fused 2-methylene pyrrolidine compound. The structural formula of the epoxy-fused 2-methylene pyrrolidine compound is shown in the specification, wherein R1 is hydrogen, methyl or phenyl, and R2 is various substituted phenyl, alkyl or heterocyclic aryl and the like. The invention also discloses a preparation method of the epoxy-fused 2-methylene pyrrolidine compound, and the epoxy-fused 2-methylene pyrrolidine compound is synthesized by reacting the sulfonyl-protected beta amino ketone derivative and the propyl-2-alkynyl sulfonium salt compound under the actionof corresponding alkali at a certain temperature. The preparation method provided by the invention has the advantages of simple operation, easily available raw materials, mild reaction conditions, good reaction functional group tolerance, excellent product yield, separation and the like.

Description

technical field [0001] The present application relates to the synthetic method of compound, relate in particular to a kind of epoxy-condensed 2-methylene pyrrolidine compound and preparation method thereof. Background technique [0002] Five-membered nitrogen-containing heterocyclic rings (pyrrolidine and pyrrole) are important structures in many natural products and biologically active molecules, such as (-)-slaframine, ABBV-3221 and other structures have a pyrrolidine or pyrrole core, and the structural formula is as follows: [0003] [0004] In particular, epoxy-fused 2-methylenepyrrolidines are a very important class of framework structures that can be used as synthons for the rapid construction of natural products containing pyrrolidine and pyrrolidone structures. Currently, only Borhan's group has reported a strategy for the construction of epoxy-fused 2-methylenepyrrolidine units from aziridine alcohols via a one-pot tandem aza-Payne / hydroamination reaction, and t...

Claims

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Application Information

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IPC IPC(8): C07D491/044
CPCC07D491/044
Inventor 祝华建贾婷婷邵加安张建康
Owner ZHEJIANG UNIV CITY COLLEGE
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