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Enzymatic resolution method for optical pure 2-amino-2'-hydroxy-1,1'-binaphthyl

An amino and hydroxyl technology, applied in the field of preparation of organic compounds, can solve the problems of high boiling point of anisole, difficult to remove, immature synthesis and splitting of NOBIN, etc., and achieve good repeatability.

Inactive Publication Date: 2012-04-11
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, in this method, it is difficult to break the amide bonds of diastereomers, and the e.e. value and yield of the product are greatly affected by the solvent and reaction temperature of the hydrolysis reaction. Anisole has a high boiling point and is difficult to remove. The resolution process requires column layers analysis, high cost and low efficiency
In short, the synthesis and separation of NOBIN is still immature and needs to be improved urgently

Method used

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  • Enzymatic resolution method for optical pure 2-amino-2'-hydroxy-1,1'-binaphthyl
  • Enzymatic resolution method for optical pure 2-amino-2'-hydroxy-1,1'-binaphthyl
  • Enzymatic resolution method for optical pure 2-amino-2'-hydroxy-1,1'-binaphthyl

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Embodiment example

[0044] The present invention will be described in detail below using examples. However, the present invention is not limited to the forms shown in the examples, and the specific embodiments can be variously changed within the range described in the specific embodiments of the present invention.

[0045] Preparation of racemic NOBIN and its derivatives

[0046] Preparation of racemic 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN)

[0047] Add 20g of 2-naphthol and 20g of 2-naphthylamine into a 500mL round-bottomed flask, add 200mL of toluene under a nitrogen atmosphere, heat to reflux for 30min, cool and filter to obtain 34g of eutectic, with a yield of 85%. Dissolve 8g of eutectic into 150ml of water, add 30g of FeCl3.6H2O, and raise the temperature to 55°C for 4-8h under the protection of nitrogen. The reaction solution was cooled to room temperature and filtered. The filter cake was washed with distilled water, dried, passed through an activated carbon column, and eluted w...

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Abstract

The invention provides an enzymatic resolution method for optical pure 2-amino-2'-hydroxy-1,1'-binaphthyl, which belongs to the field of organic compound preparation and is characterized in that the optical pure 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) is prepared by using low-cost and environmental-friendly resign cured penicillium expansum lipase (PEL) as resolution reagents by a hydrolysis and esterification two-step resolution combination method at a high yield in an enantioselectivity way. The method has the advantages that the repeatability is good, enzyme can be repeatedly used, the cost is low, the environment is protected, the energy is saved, and the method is suitable for the mass preparation of the optical pure 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN).

Description

technical field [0001] The invention belongs to the field of preparation of organic compounds. The invention relates to a method for preparing optically pure 2-amino-2'-hydroxyl-1,1'-binaphthyl (NOBIN) by enzymatic resolution. Background technique [0002] 2-Amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) is an important axial chiral ligand, which not only contains 1,1'-binaphthyl skeleton structure, but also 2-amino-2' - Hydroxyl difunctionality. Because of the large steric hindrance of the naphthalene ring, the ligand has good rigidity, and the existence of the 2-amino-2'-hydroxyl bifunctional group makes the ligand not only have the structural characteristics of amino alcohols, but also facilitate derivatization. It is the condition of an excellent chiral ligand. With the outstanding advantages of its structure, 2-amino-2'-hydroxyl-1,1'-binaphthyl (NOBIN) has attracted people's attention since it was first reported by Kocovsky in 1991 (Synlett 1991, 231), and is now A variet...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C12P13/00C07C217/94
Inventor 宋玲边广岭
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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