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
4 Cites 1 Cited by

AI-Extracted 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...
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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.

Application Domain

Organic chemistry

Technology Topic

KetonePerylene derivatives +19

Image

  • 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(22)

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, DMSO) δ 144.3, 141.9, 134.3, 132.8, 129.7, 128.9, 128.7, 127.5, 126.4, 97.8, 64.3, 63.5, 52.4, 21.1. HRMS (ESI) calcd for C 18 h 18 NO 3 S(M+H) + :328.1002,found:328.1003.
[0038] The yield situation comparison of embodiment 1 under different solvent conditions
[0039]
[0040]
[0041] The yield situation comparison of embodiment 1 under different alkali conditions
[0042]
[0043]
[0044]
[0045] Example 1 in different ratios 1:2:Cs 2 CO 3 Comparison of yield under conditions
[0046]
[0047]
[0048] The yield situation comparison of embodiment 1 at different temperatures
[0049]
[0050]

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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Classification and recommendation of technical efficacy words

  • Post-processing is simple
  • High yield
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