A kind of synthetic method of chiral carbamate and derivative thereof

A technology of carbamate and synthetic method, which is applied in the field of synthesis of chiral carbamate and its derivatives, can solve the problems of harsh reaction conditions, low reaction yield, single structure of carbamate derivatives, etc. Achieve the effects of mild reaction conditions, simple process operation and high separation yield

Active Publication Date: 2016-08-17
DALIAN UNIV OF TECH
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] 1) The reaction yield is low and the reaction conditions are harsh
[0006] 2) The structure of the obtained carbamate derivatives is single, and it is difficult to carry out functional research
[0007] 3) The current reports pay more attention to the synthesis of achiral or low enantiomeric excess carbamates, and there are few reports on the synthesis of trans carbamate derivatives with high enantiomeric excess

Method used

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  • A kind of synthetic method of chiral carbamate and derivative thereof
  • A kind of synthetic method of chiral carbamate and derivative thereof
  • A kind of synthetic method of chiral carbamate and derivative thereof

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Experimental program
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Embodiment Construction

[0023] The specific implementation manner of the present invention will be described in detail below in conjunction with the technical solutions.

[0024] In a 50 mL round bottom flask, polycarbonate, organic amine and water were dissolved in THF solution. Stir at the agreed temperature for the appointed time, stop the reaction, wait for the reaction solution to cool to room temperature, add 1M dilute hydrochloric acid, extract the organic phase three times with ethyl acetate, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, spin Dry solvent, apply column chromatography (silica gel column; developer: petroleum ether / ethyl acetate = 1 / 1-10 / 1) to separate and purify, and spin off the solvent to obtain trans-2-hydroxycarbamate and its derivatives thing.

[0025] Table 1 Ammonolysis reaction of high stereoregularity polycarbonate

[0026]

[0027]

[0028]

[0029]

[0030]

[0031] Note 1: The molar ratio of organic amine,...

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Abstract

The invention relates to a synthesis method for chiral carbamic acid ester and a derivative thereof. The synthesis method comprises the following steps: by adopting organic amine as a reaction reagent, conducting nucleophilic addition into an isotactic-structural alternative copolymer of meso epoxy alkanes and CO2 to degrade the alternative copolymer to form high-enantiomeric excess small organic molecules, namely chiral carbamic acid ester, and the derivative thereof. The synthesis has the green chemistry characteristics of being mild in conditions, high in atom economy, high in productive rate and the like; in the nucleophilic addition and degradation process of organic amine, the spatial configuration of the chiral carbon atom of polycarbonate is completely maintained, and a functional hydroxyl carbamic acid ester derivative with the enantiomeric excess being up to 99% can be generated; carbamic acid ester and the derivative thereof are important intermediates for pesticide and medicine, and have wide application prospects in complete synthesis of natural products and drug molecular design.

Description

technical field [0001] The invention relates to a method for degrading polycarbonate materials based on carbon dioxide. Organic amines are used as nucleophiles to perform nucleophilic addition to the carbonyl carbon atoms of polycarbonates and degrade them into trans carbamate derivatives. . Since the reaction does not involve the chiral environment of the polymer, the stereochemical configuration of its carbon atoms remains unchanged, and the stereoregularity of polycarbonate determines the enantiomeric excess value of small organic molecules. The reaction has green chemical characteristics such as mild conditions, atom economy and high yield, and the enantiomeric excess value of the obtained carbamate derivatives is up to 99%. In addition, the 2-position of the carbamate derivative has a hydroxyl structure, which can be functionally modified. Carbamate derivatives are important intermediates of pesticides and medicines, and have broad application prospects in the total syn...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B43/00C07D295/205C07C269/04C07C271/12C07D307/20C07D321/06C07D321/10
Inventor 吕小兵刘野任伟民何可可王萌
Owner DALIAN UNIV OF TECH
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