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Synthesis of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction

A compound and chiral compound technology, applied in the field of synthesis of chiral chroman compounds and their derivatives and precursors, can solve problems such as difficult stereoselective realization

Active Publication Date: 2016-07-13
DSM IP ASSETS BV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] It is especially difficult to stereoselectively achieve the desired chirality at the chiral carbon center at the 2-position of the chroman ring

Method used

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  • Synthesis of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction
  • Synthesis of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction
  • Synthesis of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction

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Embodiment

[0245] The present invention is further illustrated by the following experiments.

[0246] Preparation of (7R,11R)-7,11,15-trimethyl-3-oxocetanoic acid methyl ester (②)

[0247]

[0248] NaH (8.94 g, 223.5 mmol, 60% in paraffin oil, 3.0 eq.) and KH (1.08 g, 13.72 mmol, 50% in paraffin oil, 0.18 eq.) were washed with n-hexane (3x) and removed in vacuo. Remove residual solvent. The solid residue was suspended in THF (90 mL), then dimethyl carbonate (18.8 mL, 223.5 mmol, 3.0 eq.) was added. The resulting suspension was heated to reflux, then 1 mL of (6R, 1OR)-trimethylpentadecan-2-one (24.1 mL, 20.0 g, 74.5 mmol, 1.0 eq.) was added via the dropping funnel (according to WO2012 / 171969A1 in Example 19 synthesis) in THF (tetrahydrofuran) (60 mL). After 15 min, the remaining solution of (6R,10R)-trimethylpentadecan-2-one was added dropwise. Subsequently, the reaction was heated to reflux for 4 hours. After cooling by an ice bath, the reaction was quenched by the addition of...

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Abstract

The present invention relates to the preparation of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction. It has been observed that in highly stereoselective manner a methyl group can be introduced to the 2 position of chromane ring by reaction of a chromenone with Al(CH3)3 in the presence of a Cu(I) salt and specific chiral phosphoramidites. The compounds obtained are important intermediates particularly for the synthesis of chiral tocopherols.

Description

technical field [0001] The present invention relates to the field of synthesis of chiral chromane compounds and their derivatives and precursors. Background of the invention [0002] Chroman compounds represent an important class of chiral natural products and bioactive compounds. [0003] An important class of chroman compounds are members of the vitamin E group, namely all tocopherol and tocotrienol derivatives that qualitatively exhibit the biological activity of α-tocopherol (Pure & Appl. Chem., Vol. 54, No. 8, pp. 1507-1510, 1982). [0004] On the one hand, the typical synthesis of vitamin E results in a mixture of isomers. On the other hand, at the chiral center adjacent to the ether atom in the ring of the molecule (indicated by * in the formula used hereinafter in this application document) has R Tocopherols and tocotrienols in the -configuration (ie 2R-configuration) generally exhibit higher biological activity (biopotency). Particularly active are isomers of to...

Claims

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Application Information

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IPC IPC(8): C07D311/74
CPCC07D311/74
Inventor 汉斯-巩特尔·施迈兹安德里亚斯·欧乐·特马斯
Owner DSM IP ASSETS BV
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