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Preparation method of isocorydaline

A technology of isovioletine and benzyloxy, applied in the field of preparation of isovioletine, can solve the problems of large time consumption and labor, long time consumption, waste of solvent and the like, and achieve the effect of sufficient source of compounds

Inactive Publication Date: 2015-09-09
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The extraction of isochorydine generally uses plants with relatively high content such as bald sore flower, Zijinlong, and magnolia as raw materials. It is mainly extracted and separated by silica gel column chromatography, which consumes a lot of time and labor, and at the same time causes a lot of waste of solvents. , in the extraction and separation process, many toxic solvents such as chloroform, tetrahydrofuran and benzene are used to cause harm to the human body and the environment, resulting in high production costs, low efficiency, and long time-consuming

Method used

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  • Preparation method of isocorydaline
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  • Preparation method of isocorydaline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde (2) in Step A

[0048] Dissolve 10.0 g of isovanillin (1), 10.8 g of sodium acetate, and 0.34 g of iron powder in 60 mL of glacial acetic acid, stir at room temperature for 30 min, and dissolve 3.5 mL of Br 2 Dissolve in 15 mL of glacial acetic acid, slowly add dropwise to the above reaction solution, stir at room temperature for 3 h, TLC detection reaction (developing solvent, petroleum ether: acetone = 4:1, v / v), add 125 mL of ice water to the above In the reaction solution, the stirring was continued for 1 h, and the obtained white solid was recrystallized with absolute ethanol to obtain 9.9 g of light gray crystals with a yield of 65%.

[0049] HR-ESI-MS m / z 252.9457 [M+Na] + (calculated value C 8 h 7 BrNaO 3 Be 252.9471), the proton nuclear magnetic resonance spectrum of compound, the carbon spectrogram data are as follows: 1 H-NMR (400 Hz, Acetone- d 6 ): δ 10.23(s, 1H), 7.49(d, J = 8.0 Hz, 1H), 7.14 (...

Embodiment 2

[0084] Synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde (2) in Step A

[0085] Dissolve 10.0 g of isovanillin (1), 10.8 g of sodium acetate, and 0.36 g of iron powder in 60 mL of glacial acetic acid, stir at room temperature for 40 min, and dissolve 3.5 mL of Br 2 Dissolve in 15 mL glacial acetic acid, slowly add dropwise to the above reaction solution, stir at room temperature for 2 h, TLC detection reaction, (developing solvent, petroleum ether: acetone = 4:1, v / v), add 125 mL ice water In the above reaction solution, the stirring was continued for 1 h, and the filtered white solid was recrystallized with absolute ethanol to obtain 7.8 g of light gray crystals, with a yield of 52%.

[0086] Synthesis of 2-bromo-3-benzyloxy-4-methoxybenzaldehyde (3) in Step B

[0087] Dissolve 7.8 g of compound 2 in 85 mL of anhydrous DMF, and slowly add 4.3 mL of benzyl bromide dropwise to the above solution under mechanical stirring, then add 11.12 g of potassium carbonate solid powder...

Embodiment 3

[0110]Synthesis of 2-bromo-3-hydroxy-4-methoxybenzaldehyde (2) in Step A

[0111] Dissolve 10.0 g of isovanillin (1), 10.8 g of sodium acetate, and 0.34 g of iron powder in 60 mL of glacial acetic acid, stir at room temperature for 1 h, and dissolve 3.5 mL of Br 2 Dissolve in 15 mL glacial acetic acid, slowly add dropwise to the above reaction solution, stir at room temperature for 2 h, TLC detection reaction, (developing solvent, petroleum ether: acetone = 4:1, v / v), add 125 mL ice water In the above reaction solution, the stirring was continued for 1 h, and the filtered white solid was recrystallized with absolute ethanol to obtain 7.9 g of light gray crystals with a yield of 52%.

[0112] Synthesis of 2-bromo-3-benzyloxy-4-methoxybenzaldehyde (3) in Step B

[0113] Dissolve 7.9 g of compound 2 in 85 mL of anhydrous DMF, and slowly add 4.4 mL of benzyl bromide dropwise to the above solution under mechanical stirring, then add 11.3 g of potassium carbonate solid powder, reac...

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Abstract

The invention discloses a preparation method of isocorydaline. In the method, the isocorydaline is synthesized by adopting 3-hydroxyl-4-methoxybenzaldehyde (isovanillin) and 3,4-dimethoxyphenylethylamine as start raw materials through 12 steps of chemical reactions, wherein through the key Bischer-Napieralski reaction as well as the key chemical reactions such as an asymmetric hydrogenation reduction in the presence of a chiral catalyst and a coupling reaction of double benzene rings in the presence of transition metal, an organic total synthesis path of the target compound isocorydaline is established finally, and a raw material source is provided for the development of isocorydaline-based anti-cancer drugs.

Description

technical field [0001] The invention relates to a preparation method of isochorydine, which belongs to the field of organic synthesis. Background technique [0002] Isocorydine (isocorydine, transliterated as isocorydine, also known as isocorydine, which is collectively named as isocorydine in the present invention, and its chemical structure is shown in the following formula) is obtained from opium poppy such as bald acne or Zijinlong. It is an alkaloid alkaloid extracted and isolated from the family of plants, which has good pharmacological activities: such as anti-arrhythmia, vasodilator, anti-hypoxic effect, anti-cancer activity, etc. In 2010, the State Food and Drug Administration approved isochoridine hydrochloride (isocredine hydrochloride tablets) as a prescription drug (approval number: National Drug Approval H53021977) for stomach, intestine, gallbladder, pancreas, uterus, and vasospasm It is an antispasmodic analgesic. [0003] [0004] In 2012, Sun et al. tr...

Claims

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Application Information

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IPC IPC(8): C07D221/18
CPCC07D221/18
Inventor 柳军玺邸多隆钟梅
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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