Preparation method of chiral aminoheterocyclic compound and derivative thereof

A technology for aminoheterocycles and compounds, applied in the field of preparation of chiral aminoheterocycles and their derivatives, capable of solving the limitations of large-scale industrial production of 3-aminopyrrolidine and its derivatives, the starting material R-3 - tert-butoxycarbonylpyrrolidine is expensive, restricts mass production and application, and achieves short reaction time, simple and easy method, and mild conditions
CN106676142AActive Publication Date: 2017-05-17ASYMCHEM LAB TIANJIN +4
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
ASYMCHEM LAB TIANJIN
Publication Date
2017-05-17

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Abstract

The invention relates to a preparation method of a chiral aminoheterocyclic compound and a derivative thereof. The preparation method comprises the following step: under the action of an aminotransferase catalyst, a ketone compound, which is as shown in the formula I, reacts with an amino donor to obtain chiral amine as shown in the formula II. The method is simple and feasible. By generating a chiral amino compound from a corresponding ketone compound through one step, the reaction step is greatly shortened, yield reaches 70-90%, optical purity of the product is high, and ee value is stabilized at 96% and above, and the technological condition is stable. In comparison with a traditional chemical method, the method has the following advantages: reaction condition is mild; use of a strong oxidant, a strong reducer and dangerous reagents is avoided; reaction time is short; preparation cost is low; condition is mild; and the process causes little pollution to the environment. The reaction route is as shown in the specification.
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Description

technical field

[0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of chiral amino heterocyclic compounds and derivatives thereof. Background technique

[0002] 3-Aminopyrrolidine derivatives and their optical isomers are key intermediates for the synthesis of a large number of chiral drugs. There are many routes for the chemical synthesis of 3-aminopyrrolidine derivatives reported at home and abroad, including patents US4851418 and J.M.C1992 , 35, 1764 reported a five-step synthetic route to (S)-1-benzyl-3-pyrrolidinol as a starting material:

[0003]

[0004] The ee value of the product obtained by this method is 92%. Since the optical purity of the product obtained by this method is not very high, and the starting materials are relatively expensive, there is no large-scale application in China at present. At the same time, harmful reagents are used in the synthesis process Sodium azide has high requirements...

Claims

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