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A kind of method for preparing aminoalcohol derivative

A technology of derivatives and amino alcohols, which is applied in the field of preparing amino alcohol derivatives from polyol carboxylic acid esters, can solve the problems of unstable properties of epoxy compounds, difficult transportation and operation control, flammability, etc., and achieves low catalyst dosage and high The effect of selectivity, simple reaction conditions

Active Publication Date: 2021-03-19
SHANGHAI TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, epoxy compounds are usually unstable, flammable, explosive, and difficult to transport and handle

Method used

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  • A kind of method for preparing aminoalcohol derivative
  • A kind of method for preparing aminoalcohol derivative
  • A kind of method for preparing aminoalcohol derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-7

[0042]A method for preparing amino alcohol derivatives, the specific steps are: using different trifluoromethanesulfonates as catalysts, 146mg ethylene glycol diacetate 1a and 92.5mg nitrogen methyl p-toluenesulfonamide 2a as reaction substrates , the feeding amount (molar ratio) is fixed as 1a:2a=2:1, the catalyst and the reaction substrate are added in dichloroethane (1.0M) solvent, under the condition that the temperature is constant at 120°C, stir for 24 hours, nitrogen Methyl-p-toluenesulfonamide 2a replaces the ester group of ethylene glycol diacetate 1a to obtain aminoalcohol derivative 3aa, in which the amino group is derived into a sulfonamide group, and at least one carboxylic acid remains Ester group. 1 H NMR (500MHz, CDCl 3 )δ=7.67(d, J=8.1Hz, 2H), 7.32(d, J=8.0Hz, 2H), 4.21(t, J=5.7Hz, 2H), 3.28(t, J=5.7Hz, 2H) ,2.81(s,3H),2.43(s,3H),2.06(s,3H). 13 CNMR (126MHz, CDCl 3 )δ=170.8, 143.5, 134.6, 129.7, 127.3, 61.8, 48.8, 35.7, 21.5, 20.8. HR-MS (ESI-TOF) calculat...

Embodiment 8-13

[0050] A method for preparing amino alcohol derivatives, the specific steps are: using 2mol% hafnium trifluoromethanesulfonate as a catalyst, 146mg ethylene glycol diacetate 1a and 92.5mg nitrogen methyl p-toluenesulfonamide 2a as reaction substrates , the feeding amount (molar ratio) is fixed at 1a:2a=2:1, the catalyst and the reaction substrate are added to a solvent-free reaction flask or the catalyst and the reaction substrate are added to different solvents, and the temperature is constant at 120°C Under stirring reaction, nitrogen methyl p-toluenesulfonamide 2a replaces the ester group of ethylene glycol diacetate 1a to obtain aminoalcohol derivative 3aa. In the aminoalcohol derivative, the amino group is derived into a sulfonamide group, And retain at least one carboxylate group.

[0051] Table 2: Experimental parameters for solvent changes

[0052]

[0053] From Examples 8-13, it can be concluded that the reaction can obtain the optimal reaction yield after heating...

Embodiment 14-16

[0055] A method for preparing aminoalcohol derivatives, the specific steps are: using hafnium trifluoromethanesulfonate as a catalyst, ethylene glycol diacetate 1a and nitrogen methyl p-toluenesulfonamide 2a as reaction substrates, using the catalyst and reaction Add the substrate into the reaction flask, and stir the reaction for 14 hours at a constant temperature of 120°C to replace the ester group of ethylene glycol diacetate 1a with nitrogen methyl p-toluenesulfonamide 2a to obtain aminoalcohol derivatives 3aa, in the amino alcohol derivative, the amino group is derivatized into a sulfonamide group, and at least one carboxylate group remains.

[0056] Table 3: Experimental parameters for changes in feeding ratio

[0057]

[0058] From Examples 13-16, the optimal feed ratio of raw material and catalyst was obtained. Finally, we consider temperature as a single variable to investigate the effect of temperature variation on product yield.

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Abstract

The invention provides a method for preparing an amino alcohol derivative. The method is characterized in that substitution reaction is carried out on ester groups of dihydric alcohol carboxylic esteror polyhydric alcohol carboxylic ester to obtain the amino alcohol derivative, wherein the amidogen is derived into sulfonamido, and at least one carboxylic ester group remains. The method for preparing the amino alcohol derivative has the advantages that the raw materials are cheap and obtained easily, the use quantity of catalysts is low, the reaction condition is simple, and the selectivity ofproducts is high.

Description

technical field [0001] The present invention relates to a method for preparing amino alcohol derivatives from polyhydric alcohol carboxylates. Background technique [0002] Esters usually exist widely in nature in the form of oil. With the promising prospects of oil conversion in the field of renewable energy, ester conversion research is more strategic. However, the alkoxy bond-cleavage functionalization of carboxylate groups is challenging due to their excellent stability. Existing functionalization methods for cleavage of ester-based alkoxy bonds are usually limited to olefin-activated alkoxy bonds, and are catalyzed by expensive transition metals such as palladium, nickel, and ruthenium. For example, the Douglas research group used ruthenium metal catalysts to catalyze the cleavage of the alkoxy bond of aryl esters and the simultaneous insertion of alkenes to prepare a series of β-alkoxy ketones. (Angew.Chem.Int.Ed., 2011, 50, 1882) The conversion conditions for alkyl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/17C07C311/29C07C303/40C07D275/06
CPCC07C303/40C07C311/17C07C311/29C07D275/06
Inventor 李智刘华
Owner SHANGHAI TECH UNIV
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