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Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of acids

A technology of chiral centers and chiral compounds, applied in the field of synthesis of tocopherols and tocotrienols

Active Publication Date: 2016-02-24
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, considering the configuration of the respective 2-positions of the chroman and chromanone rings, this procedure results in a racemic mixture

Method used

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  • Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of acids
  • Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of acids
  • Formation of chiral 4-chromanones using chiral pyrrolidines in the presence of acids

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Experimental program
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Embodiment

[0201] The present invention is further illustrated by the following experiments.

[0202] use a different acid

[0203] At 23 °C, in a 20 mL round bottom flask equipped with a magnetic stir bar, heating device, water separator and argon supply, 0.5 mmol 2-acetyl-3,5,6-trimethylhydroquinone and 0.795 mmol The acids shown in Table 1 were suspended in 2.5 mL (23.5 mmol) toluene. Then, 0.514 mmol of E,E-farnesylacetone was added, and finally 0.795 mmol of (S)-2-(methoxymethyl)pyrrolidine was added. The reaction mixture was then stirred at the temperature indicated in Table 1 for the time indicated in Table 1. When heated to 120°C, water was distilled off and the reaction mixture turned brown. After the indicated time, the reaction mixture was cooled to 23 °C. Then 1 mL of 2N HCl was added and the mixture was transferred to a separatory funnel and shaken well. The toluene phase was separated and washed with several 10 mL portions of water until a neutral aqueous phase was o...

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Abstract

The present invention relates to a synthesis of chromanones or chromanes in a stereospecific matter in view of the 2-position in the chromanone or chromane ring. It has been found that this synthesis is particularly possible in the presence of a chiral compound of a specific type and of at least one Bransted acid or in the presence a specific chiral compound having a Bransted acid functional group in the molecule.

Description

technical field [0001] The present invention relates to the field of synthesis of tocopherols and tocotrienols. Background of the invention [0002] Chromone compounds represent an important class of chiral natural products and bioactive compounds. An important class of chroman compounds is vitamin E and its esters. Typically, vitamin E is commercialized in its ester form because the latter exhibit enhanced stability. [0003] On the one hand, the typical technical synthesis of vitamin E results in a mixture of isomers. On the other hand, it has been shown that the chiral center adjacent to the ether atom in the ring of the molecule (indicated by * in the formulas used later in this text) has R compared to the corresponding isomer with the S-configuration Tocopherols and tocotrienols in the -configuration (ie 2R-configuration) generally exhibit higher biological activity (biopotency). Isomers of tocopherol which have the natural configuration at all chiral centers are es...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22
CPCC07D311/22C07B2200/09
Inventor 乔纳森·艾伦·米德洛克尤拉·莱提诺伊斯托马斯·内切尔沃纳尔·邦拉蒂
Owner DSM IP ASSETS BV
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