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Tetrahydroisoquinoline compound intermediate, and preparation method and application thereof

A technology for tetrahydroisoquinoline and compounds, which is applied in the field of tetrahydroisoquinoline compound intermediates, can solve the problems of high price, low total yield, numerous and complicated reaction steps, etc., and achieves low-cost raw materials, simple preparation methods, The effect of high bioavailability

Active Publication Date: 2015-10-14
SHENZHEN NEPTUNUS INTERLONG BIO TECHN HLDG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this method for preparing tetrahydroisoquinolines, the reaction steps are numerous and complicated, the total yield is low, and the source of raw materials for preparing the tetrahydroisoquinolines is limited and expensive

Method used

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  • Tetrahydroisoquinoline compound intermediate, and preparation method and application thereof
  • Tetrahydroisoquinoline compound intermediate, and preparation method and application thereof
  • Tetrahydroisoquinoline compound intermediate, and preparation method and application thereof

Examples

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preparation example Construction

[0063] The preparation method of the tetrahydroisoquinoline compound of the present invention comprises the following steps: taking the halogenated aromatic compound as the starting material, undergoing nucleophilic substitution, addition, hydroxyl elimination and protecting group removal reactions to obtain a chiral The tetrahydroisoquinoline compound of amine, preparation process is as follows.

[0064]

[0065] The preparation method of the tetrahydroisoquinoline compound specifically includes the following steps.

[0066] A. Preparation of D-cyclic aldehydes.

[0067] The preparation of the D-cyclic aldehyde is as follows.

[0068]

[0069] (a) Preparation of N-benzyloxycarbonyl-D-serine methyl ester (N-Cbz-D-serine methyl ester).

[0070] The raw material compound 5 was mixed with methanol (CH 3 OH), thionyl chloride (SOCl 2 ) reaction to generate D-serine methyl ester hydrochloride.

[0071] In the present embodiment, the raw material compound 5 is D-serine, ...

Embodiment 1

[0102] Example 1 Preparation of (S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol

[0103] The following embodiments will help to further understand the present invention, but are not limited to the content of the present invention. The preparation process of the tetrahydroisoquinoline compound (S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol of the present invention is as follows.

[0104]

[0105] A. To prepare N-benzyloxycarbonyl-D-serinaldehyde, the preparation process is as follows.

[0106]

[0107] (a) Preparation of N-Cbz-D-serine methyl ester.

[0108] 200 mL CH 3 OH was placed in a 250 mL three-neck flask, cooled to 0 °C, and 22.0 mL SOCl 2 Add dropwise into methanol, react for 30 min, add 21.1 g of D-serine into the reaction system, slowly rise to room temperature and react overnight. The reaction solution was spin-dried to obtain 30 g of D-serine methyl ester hydrochloride with a yield of 98%.

[0109] Take 15.5 g of D-serine methyl este...

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Abstract

The invention provides a tetrahydroisoquinoline compound with the following structural general formula I. The invention also provides application of the above tetrahydroisoquinoline compound as an intermediate for the preparation of tetrahydroisoquinoline alkaloid natural medicaments. The invention further provides a method for preparing the tetrahydroisoquinoline compound. The method uses a halogenated aromatic compound as a starting material, and conducts nucleophilic substitution, addition, hydroxy elimination and protecting group elimination reaction, thereby obtaining the tetrahydroisoquinoline compound with chiral amine.

Description

technical field [0001] The invention relates to a tetrahydroisoquinoline compound intermediate, its preparation method and its application. Background technique [0002] The tetrahydroisoquinoline alkaloid naphthyridinomycin (NDM) is a class of organic molecules with a unique chemical structure and good anti-tumor activity, widely distributed in nature, such as Magnoliaceae, Lauraceae, Poppyaceae and other plants . The first case of tetrahydroisoquinoline alkaloids was isolated from the soil-derived Portuguese Streptomyces lusitanus AYB-1206 by Canadian scientist Kluepfel et al. in 1974. However, with the continuous deepening of the research on the chemical components of plants, more and more new tetrahydroisoquinoline natural products have been extracted. Due to the unique chemical structure, low content and significant biological activity of this type of natural products, People began to pay attention to the precursor source and biosynthetic pathway of the tetrahydroisoq...

Claims

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Application Information

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IPC IPC(8): C07C217/64C07C213/02
CPCY02P20/55
Inventor 史雷苟宝权夏吾炯
Owner SHENZHEN NEPTUNUS INTERLONG BIO TECHN HLDG
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