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Method for synthesizing allylamine derivative

A technology for the preparation of allylamine derivatives, which is applied in the field of preparation of allylamine derivatives, can solve the problems of narrow applicability and poor atom economy, and achieve the effects of simple operation, avoiding subsequent processing, and convenient operation and processing

Active Publication Date: 2021-03-26
WESTLAKE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the shortcomings of the existing substrates, such as narrow applicability, the need for an additional equivalent of reducing agent, and poor atom economy, the present invention provides a method to directly realize the alkynylation reaction at the α-position of the amine, and efficiently construct polymorphic compounds with diverse structures. Allylamine Derivatives

Method used

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  • Method for synthesizing allylamine derivative
  • Method for synthesizing allylamine derivative
  • Method for synthesizing allylamine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of (E)-2,4,6-trimethyl-N-(1,2,3-triphenylallyl)benzosulfonamide

[0028]

[0029] In a nitrogen atmosphere, add raw material 1a (0.1mmol, 28.9mg), raw material 2a (0.2mmol, 35.6mg), K 3 PO 4 (0.04mmol, 8.4mg), Ni(cod) 2 (0.007mmol, 1.9mg), and PCy 3 (0.014mmol, 3.92mg), and finally Dioxane (0.5mL) was added, stirred at 120°C for 24 hours, cooled to room temperature, concentrated, and directly separated by column chromatography to obtain the target product 3a with a yield of 92%, 43.0mg. 1 H NMR (500MHz, CDCl 3 ) δ7.24(m,5H),7.20-7.17(m,1H),7.13-7.10(m,2H),7.06-7.01(m,3H),6.85(s, 2H),6.77-6.74(m, 4H), 6.52(s, 1H), 5.31(d, J=6.5Hz, 1H), 4.94(d, J=6.5Hz, 1H), 2.52(s, 6H), 2.23(s, 3H); 13 C NMR (126MHz, CDCl 3 )δ142.1, 140.1, 139.1, 138.9, 137.5, 135.9, 134.5, 131.9, 129.4, 129.2, 129.2, 128.5, 128.5, 127.8, 127.8, 127.6, 127.4, 126.9, 64.2, 23.0-HRMS, 20.8 / z calcd.for C 30 h 29 NO 2 SNa [M+Na] + :490.1817, found 490.1818.

[0030] Scale-up prepa...

Embodiment 2

[0033] Preparation of (E)-N-(2,3-diphenyl-1-(o-tolyl)allyl)-2,4,6-trimethylbenzonesulfonamide

[0034]

[0035] In a nitrogen atmosphere, add raw material 1b (0.1mmol, 30.3mg), raw material 2a (0.2mmol, 35.6mg), K 3 PO 4 (0.04mmol, 8.4mg), Ni(cod) 2 (0.007mmol, 1.9mg), and PCy 3(0.014mmol, 3.92mg), and finally Dioxane (0.5mL) was added, stirred at 120°C for 24 hours, cooled to room temperature, concentrated, and directly separated by column chromatography to obtain the target product 3b with a yield of 87%, 41.8mg. 1 H NMR (500MHz, CDCl 3 ) δ7.32-7.27(m,1H),7.20-6.97(m,9H),6.87-6.84(m,2H),6.81(s,2H),6.70-6.66(m,2H),6.36(s, 1H), 5.52(d, J=5.1Hz, 1H), 4.88(d, J=5.1Hz, 1H), 2.52(s, 6H), 2.21(s, 3H), 2.14(s, 3H); 13 C NMR (126MHz, CDCl 3 )δ142.0, 139.8, 138.8, 138.3, 137.0, 136.0, 135.9, 134.5, 131.9, 130.6, 129.1, 129.0, 128.9, 128.6, 127.8, 127.7, 127.5, 127.3, 126.8, 0, 123.2, 30; MS (ESI-TOF)m / z calcd. for C 31 h 31 NO 2 SNa[M+Na] + :504.1973,found 504.1975.

Embodiment 3

[0037] Preparation of (E)-N-(1-(2-fluorophenyl)-2,3-diphenylallyl)-2,4,6-trimethylbenzenesulfonamide

[0038]

[0039] In a nitrogen atmosphere, sequentially add raw material 1c (0.1mmol, 30.7mg), raw material 2a (0.2mmol, 35.6mg) to the reaction flask, K 3 PO 4 (0.04mmol, 8.4mg), Ni(cod) 2 (0.007mmol, 1.9mg), and PCy 3 (0.014mmol, 3.92mg), and finally Dioxane (0.5mL) was added, stirred at 120°C for 24 hours, cooled to room temperature, concentrated, and directly separated by column chromatography to obtain the target product 3c with a yield of 73%, 35.4mg. 1 H NMR (500MHz, CDCl 3 ) δ7.22-7.11(m,5H),7.06-6.85(m,7H),6.77(s,2H),6.76-6.72(m,2H),6.41(s,1H),5.52(d,J= 6.8Hz, 1H), 5.10(d, J=7.0Hz, 1H), 2.48(s, 6H), 2.22(s, 3H); 13 C NMR (126MHz, CDCl 3 )δ160.1(d, J=247.0Hz), 142.0, 139.5, 138.9, 137.6, 135.8, 133.7, 131.8, 129.5, 129.4(d, J=8.5Hz), 129.2, 129.1(d, J=3.8Hz) , 129.0,128.7,127.8,127.6,127.0,126.5(d,J=12.7Hz),124.0(d,J=3.5Hz), 115.4(d,J=21.6Hz),58.3(d,J=2.5Hz) ...

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Abstract

The invention discloses a method for synthesizing an allylamine derivative. The method comprises the following steps: implementing hydrogen transfer in reactant amine by using a metal nickel catalyst,and implementing a coupling reaction between the reactant amine and alkyne in the same catalytic system to construct allylamine; the reaction is well applicable to amine compounds and alkyne, and canrealize the construction of chiral allylamine. According to the method, an additional reducing agent does not need to be added as a hydrogen source, an additional guide group does not need to be introduced, the scale is enlarged to gram level, and the yield can still be kept.

Description

technical field [0001] The invention relates to the technical field of dehydrogenation reduction coupling reaction, in particular to a method for preparing allylamine derivatives starting from common non-guiding amines and alkynes. Background technique [0002] The structure of allylamine widely exists in functional materials, active drug molecules and many chiral ligands, and is an important type of organic structure skeleton. Therefore, how to efficiently prepare allylamine derivatives with diverse structures has high research and application value . [0003] At present, allylamine derivatives are mainly synthesized by the following methods: [0004] (1) Under the catalysis of alkenyl boron reagent and imine transition metal, allylamine derivatives are obtained. This reaction needs to use noble metal rhodium (Rh) as a catalyst, and the reaction substrate imine is unstable and easy to decompose, and the synthesis is relatively inconvenient; alkenyl borate also needs to be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/40C07D307/52C07D333/20C07D335/02C07F7/18C07F9/6568C07F7/10C07B37/02C07C311/16C07C311/17C07C311/19C07C311/18
CPCC07C303/40C07F7/1892C07F7/083C07F9/65683C07D335/02C07D333/20C07D307/52C07B37/02C07C2601/04C07C2601/14C07C311/16C07C311/17C07C311/19C07C311/18Y02P20/584
Inventor 石航李伦刘玉成
Owner WESTLAKE UNIV
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