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Preparation process for chiral (R)-1-ferrocenyl ethyl dimethylamine

A ferrocenyl ethyl dimethylamine and preparation technology technology, applied in the field of preparation technology of 1-ferrocenyl ethyl dimethylamine, can solve problems such as low yield and complicated operation process, and achieve yield High efficiency, simple operation process, and high ee value

Inactive Publication Date: 2014-04-30
ZHEJIANG ZHONGSHAN CHEM IND GRP
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Problems solved by technology

In the methods of the prior art, the chiral center of ferrocenyl ethyl dimethylamine is obtained by the method of chiral resolution, the yield is very low, and the operation process is complicated; or use another very expensive chiral center Ligands and catalysts to asymmetrically hydrogenate carbonyl groups to obtain their chiral centers

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  • Preparation process for chiral (R)-1-ferrocenyl ethyl dimethylamine

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Embodiment 1

[0021] The preparation process embodiment 1 of a kind of chiral (R)-1-ferrocenyl ethyl dimethylamine of the present invention, its preparation step comprises successively:

[0022] Step 1, 11.4g (0.05mol) acetylferrocene and 250ml concentration are the tetrahydrofuran (THF) solution of the TarB-H of 0.4mol / L (0.1mol) adding the volume with magnetic stirring, low temperature thermometer and drying tube is In a 500ml three-neck flask, stir in ice bath to 0°C for 15min, add 3.8g (0.1mol) sodium borohydride (NaBH 4 ), stirred at room temperature for 2h, then transferred the reaction solution into a beaker with a volume of 1L, slowly added 300ml of hydrochloric acid (HCl) with a concentration of 1mol / L to quench the reaction, added 28g of sodium hydroxide (NaOH) solid to adjust the pH value to 12, and continue to stir for 30min, stand still for liquid separation, extract the aqueous phase with n-hexane (200ml×3), combine the organic phases, wash with saturated aqueous sodium chlori...

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a preparation process for chiral (R)-1-ferrocenyl ethyl dimethylamine. According to the preparation process, acetylferrocene is used as a raw material and is asymmetrically reduced to obtain R-architectonic ferrocenyl ethanol; then optically-pure (R)-1-ferrocenyl ethyl dimethylamine is obtained by an esterification and amination one-pot method. The method does not need resolution so that the synthesis yield of the (R)-1-ferrocenyl ethyl dimethylamine is greatly improved; the preparation process has the characteristics of moderate reaction conditions, high optical purity and the like; the synthesis yield of a ferrocene diphosphine ligand which takes the (R)-1-ferrocenyl ethyl dimethylamine as a key intermediate is improved; te production cost is reduced and the preparation process is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation process of chiral (R)-1-ferrocenylethyldimethylamine. Background technique [0002] Chiral ferrocene bisphosphine ligands are important ligands in asymmetric catalytic hydrogenation reactions, and have been widely used in industrial asymmetric hydrogenation. (R)-1-ferrocenylethyldimethylamine is a key intermediate of this kind of chiral ligands, and it is also the focus and research hotspot in the field of chiral ligands at home and abroad. [0003] The key point about the synthesis of (R)-1-ferrocenylethyldimethylamine lies in the construction of its chiral center. In the methods of the prior art, the chiral center of ferrocenyl ethyl dimethylamine is obtained by the method of chiral resolution, the yield is very low, and the operation process is complicated; or use another very expensive chiral center Ligands and catalysts to asymmetrically hydrogenate c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
Inventor 王涛杨华春石雅义叶炳贤杨洁刘海飞
Owner ZHEJIANG ZHONGSHAN CHEM IND GRP
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