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Preparation method of metaraminol bitartrate

A technology of metaraminol bitartrate and tartaric acid, which is applied in the field of preparation of metaraminol tartrate, can solve the problems of high cost of chiral resolution and no chiral selectivity of metaraminol bitartrate, so as to reduce the cost of splitting and avoid splitting Good separation of isomers and chiral selectivity

Pending Publication Date: 2022-05-13
汉瑞药业(荆门)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] From the above review, it can be seen that the current synthetic strategies for metaraminol bitartrate have the disadvantages of no chiral selectivity and high cost of chiral resolution.

Method used

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  • Preparation method of metaraminol bitartrate
  • Preparation method of metaraminol bitartrate
  • Preparation method of metaraminol bitartrate

Examples

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Comparison scheme
Effect test

Embodiment 1

[0026] A kind of preparation method of metaraminol tartrate disclosed by the invention, its synthetic route is as follows:

[0027]

[0028] Where [M] is a conventional organic basic reagent, such as triethylamine, DBU, DIPEA, etc.; [Pd] is a palladium catalyst, such as palladium carbon, palladium hydroxide carbon. Specific steps are as follows:

[0029] S1: Take the structural formula as The compound 1 is reacted with N,O-dimethylhydroxylamine hydrochloride in a solvent, and a base is added during the reaction to obtain the structural formula: Compound 2.

[0030] The preparation steps of compound 2 are as follows: add 100ml DCM to the reaction flask, then add 10g compound 1, stir and cool down to 0-10°C, then dropwise add 10g liquid triethylamine, add 6g N,O- dimethyl hydroxylamine salt acid salt, keep warm at 0-10°C, stir for 4 hours; add 300ml 1mol / L hydrochloric acid solution dropwise after the controlled reaction in TLC (thin-layer chromatography) to adjust pH≈1,...

Embodiment 2

[0038] The difference between the preparation method of metaraminol tartrate disclosed in this example and Example 1 is that the solvent uses toluene or dioxane.

Embodiment 3

[0040] The difference between the preparation method of metaraminol bitartrate disclosed in this example and Example 1 is that DBU or DIPEA is used as the base.

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Abstract

The invention discloses a preparation method of metaraminol bitartrate, which sequentially comprises the following steps: reacting a compound 1 with N, O-dimethyl hydroxylamine hydrochloride to obtain a compound 2, and adding alkali in the reaction process; reacting the compound 2 obtained in the previous step with a compound 3 to obtain a compound 4; reacting the compound 4 obtained in the previous step with aluminum isopropoxide to obtain a compound 5; and adding the compound 5 obtained in the previous step into a solvent, adding a metal catalyst, introducing hydrogen for debenzylation to obtain m-hydroxylamine, then adding tartaric acid, and stirring and filtering to obtain metaraminol bitartrate. The method is short in route, aluminum isopropoxide is used for asymmetric reduction, chiral selectivity is good, isomer resolution is avoided, and cost is saved.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical production, and in particular relates to a preparation method of metaraminol bitartrate. Background technique [0002] Metaraminol Bitartrate is the bitartrate of Metaraminol Bitartrate. It is an α-adrenergic receptor agonist developed by Fresenius Kabi Company in the United States. It mainly acts on α-receptors. It is suitable for early treatment of shock and prevents spinal Acute hypotension during internal block anesthesia. [0003] CN103739504 has reported a kind of synthetic method of metaraminol tartrate as follows: [0004] [0005] The nitroethane used in this route is inflammable and explosive, relatively dangerous, and not suitable for production scale-up. Moreover, this route has no chiral selectivity, and the cost of chiral resolution is very high. [0006] CN107311875A has reported another kind of synthetic method of metaraminol tartrate: [0007] [0008] This route ...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C213/08C07C215/60C07C217/60C07C51/41C07C59/255C07C259/06C07C221/00C07C225/16C07B53/00
CPCC07C213/00C07C213/08C07C217/60C07C51/412C07C259/06C07C221/00C07B53/00C07B2200/07C07C215/60C07C59/255C07C225/16
Inventor 李堃
Owner 汉瑞药业(荆门)有限公司
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