Synthetic method for methyl caulophine

A technology of methyl rhodochrous and dimethylamino, which is applied in the field of synthesizing methyl rhodochrine, can solve the problems that the research on total synthesis of rhodochrine is still blank, and the natural sources of rhodokinine are limited, etc., and achieves good results. Application prospect and research value, cheap and easy availability of reagents, mild reaction conditions

Active Publication Date: 2015-10-28
XI AN JIAOTONG UNIV
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Problems solved by technology

[0004] However, the natural sources of ramectine are limited, and so far, the research on the total synthesis of ramectine and its derivatives is still blank

Method used

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  • Synthetic method for methyl caulophine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Step Ⅰ: Compound 2: Synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde

[0040] Weigh 10.00g (65.73mmol) of isovanillin, dissolve it in a 500ml round bottom flask with 200ml glacial acetic acid, add 10.78g (131.45mmol) of sodium acetate, 0.37g (6.57mmol) of iron powder; then take 3.4ml of liquid bromine (65.73mmol) was added to a constant-pressure low-liquid funnel filled with 20ml of glacial acetic acid, and slowly added dropwise to a round-bottomed flask under ice-bath stirring conditions. Add 500ml of ice water, stir for a few minutes, let stand for 10 minutes, filter with suction, wash with ice water until there is no taste of glacial acetic acid, dry and weigh the filter cake to obtain 13.40g of white solid, which is 2-bromo-3-hydroxy-4-methoxy phenylbenzaldehyde (compound 2), yield 88.74%; m.p.206-207°C.

[0041] Step Ⅱ: Compound 3: Synthesis of 2-bromo-3,4-dimethoxybenzaldehyde

[0042] Weigh 10.00g (43.28mmol) of compound 2, dissolve it in a 500ml round-bott...

Embodiment 2

[0065] Step Ⅰ: Compound 2: Synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde

[0066] Weigh 10.00g (65.73mmol) of isovanillin, dissolve it in a 500ml round bottom flask with 200ml glacial acetic acid, add 10.78g (131.45mmol) of sodium acetate, 0.37g (6.57mmol) of iron powder; then take 3.4ml of liquid bromine (65.73mmol) was added to a constant-pressure low-liquid funnel filled with 20ml of glacial acetic acid, and slowly added dropwise to a round-bottomed flask under ice-bath stirring conditions. Add 500ml of ice water, stir for a few minutes, let stand for 10 minutes, filter with suction, wash with ice water until there is no taste of glacial acetic acid, dry and weigh the filter cake to obtain a white solid, which is 2-bromo-3-hydroxy-4-methoxybenzene Formaldehyde (Compound 2); m.p. 206-207°C.

[0067] Step Ⅱ: Compound 3: Synthesis of 2-bromo-3,4-dimethoxybenzaldehyde

[0068] Weigh 10.00g (43.28mmol) of compound 2, dissolve it in a 500ml round bottom flask with dry ac...

Embodiment 3

[0091] Step Ⅰ: Compound 2: Synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde

[0092] Weigh 10.00g (65.73mmol) of isovanillin, dissolve it in a 500ml round bottom flask with 200ml glacial acetic acid, add 10.78g (131.45mmol) of sodium acetate, 0.37g (6.57mmol) of iron powder; then take 3.4ml of liquid bromine (65.73mmol) was added to a constant-pressure low-liquid funnel filled with 20ml of glacial acetic acid, and slowly added dropwise to a round-bottomed flask under ice-bath stirring conditions. Add 500ml of ice water, stir for a few minutes, let stand for 10 minutes, filter with suction, wash with ice water until there is no taste of glacial acetic acid, dry and weigh the filter cake to obtain a white solid, which is 2-bromo-3-hydroxy-4-methoxybenzene Formaldehyde (Compound 2); m.p. 206-207°C.

[0093] Step Ⅱ: Compound 3: Synthesis of 2-bromo-3,4-dimethoxybenzaldehyde

[0094] Weigh 10.00g (43.28mmol) of compound 2, dissolve it in a 500ml round bottom flask with dry ac...

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Abstract

The invention provides a synthetic method for methyl caulophine. The method comprises the following steps: with isovanillin and p-hydroxyanisole as raw materials, successively subjecting isovanillin to bromination and methylation so as to obtain 2-bromo-3,4- dimethoxy benzaldehyde; successively subjecting p-hydroxyanisole to acetylation, bromination, hydrolyzation, allyl etherification, Claisen rearrangement and methylation so as to obtain 1-allyl-4-bromo-2,5-dimethoxybenzene; successively subjecting the obtained 1-allyl-4-bromo-2,5-dimethoxybenzene and 2-bromo-3,4- dimethoxy benzaldehyde to Grignard reaction, ruthenium chloride/sodium periodate double-bond oxidation, reductive amination, pyridine chlorodichromate oxidation and intramolecular coupling so as to obtain 3-(2-(N,N-dimethylamino)methyl)-1,4,5,6-tetramethoxyl-9-H-fluorene-9-ketone, i.e. the method for synthesizing methyl caulophine is completed. The method in the invention has the advantages of mild reaction conditions, simple operation, easily-available raw materials and reagents, etc., and is suitable for large-scale production of pharmaceutical enterprises

Description

technical field [0001] The invention belongs to the technical field of synthesis of medicinal compounds, and in particular relates to a method for synthesizing methyl ramectine. Background technique [0002] Ermectine (3-(2-(dimethylamino)ethyl)-4,5-dihydroxy-1,6-dimethoxy-9H-fluoren-9-one, caulophine) is isolated and purified from the medicinal plant Rhizoma chinensis A fluorenone alkaloid with a novel structure. [0003] Now through myocardial cell membrane chromatography experiment, isolated frog heart perfusion experiment and SD rat myocardial ischemia model experiment, it has been confirmed that ramectine has anti-myocardial ischemia activity, can significantly reduce the size of myocardial infarction, and can be used as a therapeutic agent for the development of myocardial ischemia. Novel lead compounds for blood disease drugs. [0004] However, the natural sources of ramectine are limited, and so far, the research on the total synthesis of ramectine and its derivati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/18C07C221/00
Inventor 王嗣岑张杰沈秀秀贺浪冲潘晓艳
Owner XI AN JIAOTONG UNIV
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