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Formation of chiral 4-chromanone using chiral pyrrolidine in the presence of phenol or thiophenol

A technology of thiophenols and chiral centers, applied in organic chemistry, organic chemistry methods, etc.

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-chromanone using chiral pyrrolidine in the presence of phenol or thiophenol
  • Formation of chiral 4-chromanone using chiral pyrrolidine in the presence of phenol or thiophenol
  • Formation of chiral 4-chromanone using chiral pyrrolidine in the presence of phenol or thiophenol

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Experimental program
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Embodiment

[0168] The present invention is further illustrated by the following experiments.

[0169] use different additives

[0170] At 23 °C (or 40 °C), 0.5 mmol 2-acetyl- 3,5,6-trimethylhydroquinone (or 2-acetyl-3,5,6-trimethylhydroquinone 4-O-acetate) and 0.795 mmol of additives shown in Table 1 were suspended in 2.5 mL (23.47mmol) in 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 23°C (or 40°C) 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 at 120°C, the reaction mixture was cooled to 23°C. Then 1 mL of 2N aqueous 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 obtained. The organic layer was dried over so...

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Abstract

The present invention relates to a synthesis of chromanone or chromane in a stereo-specific 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 formula of a specific type and of at least one phenol or thiophenol.

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 尤拉·莱提诺伊斯托马斯·内切尔
Owner DSM IP ASSETS BV
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