Preparation method of (S)-N-BOC-3-hydroxypiperidine

A technology of -N-BOC-3-, hydroxypiperidine, which is applied in the field of preparation of -N-BOC-3-hydroxypiperidine, can solve the problems of cumbersome post-processing, high price, and high price of biological enzymes, and achieve the preparation method Environmental protection, good product quality, high reaction safety effect
CN110759853AActive Publication Date: 2020-02-07上海科利生物医药有限公司
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
上海科利生物医药有限公司
Publication Date
2020-02-07

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Abstract

The invention provides a preparation method of (S)-N-BOC-3-hydroxypiperidine. The preparation method comprises the following steps: carrying out a reaction on (S)-epichlorohydrin with a 2-chloroethylmagnesium bromide Grignard reagent to obtain (S)-1,5-dichloro-2-pentanol, carrying out an intramolecular cyclization reaction in the presence of an alkaline substance to generate (S)-5-chloro-1,2-epoxypentane, carrying out a reaction on the (S)-5-chloro-1,2-epoxypentane with an ammonia solution to generate (S)-1-amino-5-chloro-2-pentanol, then carrying out an intramolecular cyclization reaction onthe (S)-1-amino-5-chloro-2-pentanol to obtain (S)-3-hydroxypiperidine, and finally carrying out a reaction with BOC anhydride to obtain the product (S)-N-BOC-3-hydroxypiperidine. The preparation method disclosed by the invention has the advantages of short synthesis route, few side reactions and high yield; the product has good quality and is convenient for purification. The raw materials are easily available and has low price; the reaction conditions are mild; and safety is high. The preparation method is environmentally friendly, is simple and practice, and is suitable for industrial batchproduction.
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Description

technical field

[0001] The invention belongs to the field of compound synthesis and relates to a preparation method of (S)-N-BOC-3-hydroxypiperidine. Background technique

[0002] (S)-N-Boc-3-hydroxypiperidine is an important pharmaceutical intermediate, widely used in the synthesis of analgesic, antipsychotic, antitumor drugs, etc. Synthesis of flatness, antimalarial drugs tembranine and anomaly. At present, optically active (S)-N-Boc-3-hydroxypiperidines can be obtained by chemical methods or enzymatic biological methods. However, most of the products synthesized by chemical methods are para-3-hydroxypiperidines or Therefore, N-Boc-3-hydroxypiperidine needs to be split in the synthesis process, and the limitation of the split method is that the yield is low, and the separation and extraction are also complicated, which is not conducive to industrial production. However, the biological method takes enzymatic catalysis as the main method. Through the asymmetric reduction o...

Claims

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