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(s)-(-)-5-tributyltin-n-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide preparation method

A technology of dimethoxybenzamide and dimethoxybenzoic acid, applied in the field of organic synthesis

Inactive Publication Date: 2007-08-01
JIANGSU INST OF NUCLEAR MEDICINE
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Problems solved by technology

[0011] At present, there is no (s)-(-)-N-[(1-allyl-2-pyrrolidinyl)methyl]-5-iodo-2,3-dimethoxybenzamide (3 ) and (s)-(-)-5-tributyltin-N-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide (4) Report on the preparation method

Method used

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  • (s)-(-)-5-tributyltin-n-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide preparation method

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Embodiment 1

[0031] Preparation of (s)-(-)-N-[(1-allyl-2-pyrrolidinyl)methyl]-5-iodo-2,3-dimethoxybenzamide (3).

[0032]According to document 2 and document (Xu Yuping, Pan Donghui, Yang Min, the preparation of (s)-1-allyl-2-aminomethyltetrahydropyrrolidine, Chinese Journal of Pharmaceutical Industry, 2006, 37 (2): 84) 5-iodo-2,3-dimethoxybenzoic acid (1) and (s)-1-allyl-2-aminomethyltetrahydropyrrolidine (2) were obtained respectively.

[0033] a) 5-iodo-2,3-dimethoxybenzoic acid (1) (1.0g, 3.7mmol), (s)-1-allyl-2-aminomethyltetrahydropyrrolamine (2) ( 0.8g, 5.70mmol) and pyridine were added to chloroform, dicyclohexylcarbodiimide (DCC) (1.0g, 4.8mmol) was added at 0°C, stirred for 4 hours, filtered, and the filtrate was washed with saturated sodium carbonate solution and water successively Dry over anhydrous magnesium sulfate, filter, concentrate the filtrate to dryness, and the residue is subjected to column chromatography (developing solvent: dichloromethane:methanol=10:1, Rf0.7) to ...

Embodiment 2

[0036] Preparation of (s)-(-)-5-tributyltin-N-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide (4).

[0037] (s)-(-)-N-[(1-allyl-2-pyrrolidinyl)methyl]-5-iodo-2,3-dimethoxybenzamide (3) (0.58g, 1.34mmol), dissolved in triethylamine, added (Ph 3 P 4 )Pd (0.08g, 0.046mmol), PdAc (0.04g, 0.198mmol) and bistributyltin (1.1ml, 2.1mmol). The reaction was refluxed for 24 hours, and after cooling, the solvent was distilled off. The residue was subjected to column chromatography (developing solvent: dichloromethane:methanol=10:1, Rf0.6) to obtain light yellow oil (s)-(-)-5-tributyltin-N-[(1-allyl yl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide (4) (0.65 g, 82%). The structure was confirmed by elemental analysis, MS, NMR and IR.

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Abstract

The invention discloses a making method of (s)-(-)-5-tributyl tin-N-[(1-allyl-2-pyrrolidyl) methyl]-2, 3-dimethoxy benzamide in the organic synthetic technical domain, which comprises the following steps: a) adopting 5-iodine-2, 3-dimethoxy benzene carbonic acid and (s)-1-allyl-2-methylamino pyrrolidone as raw material; acylating dicyclo hexylcar bodiimide and pyridine; or b) acylating oxalyl chloride and N, N-dimethyl formamide to make (s)-(-)-N-[(1-allyl-2-pyrrolidyl) methyl]-5-iodine-2, 3-dimethoxy benzamide with receiving rate at 85% and 91% separately; reacting with ditributyl tin catalyzed by (Ph3P4)Pd and PdAc to produce the product with receiving rate at 82% as important marked primer of 123I-nalepride to make SPECT imaging agent marked by iodine [123].

Description

technical field [0001] The preparation method of (s)-(-)-5-tributyltin-N-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxybenzamide belongs to organic The field of synthetic technology. Background technique [0002] With economic and social development, neuropsychiatric diseases have become the first in the total burden of disease, so early diagnosis of neuropsychiatric diseases is extremely important. Recent studies have shown that many neuropsychiatric diseases (Parkinson's disease, Huntington's disease, Wilson's disease, etc.) 2 Abnormal expression of receptors. [0003] Single-photon emitter tomography (SPECT) can be used for dopamine D 2 Non-invasive imaging of receptors with high sensitivity and good resolution. Currently, 123 I-epidepride[(s)-(-)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-iodo[ 123 I]-2,3-dimethoxybenzamide] is dopamine D 2 The preferred SPECT imaging agent for receptors. [0004] 123 I-nalepride[(s)-(-)-N-[(1-allyl-2-pyrrolidinyl)methyl]-5-iodo[ 123...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09A61K51/04A61K101/02
Inventor 杨敏徐宇平潘栋辉
Owner JIANGSU INST OF NUCLEAR MEDICINE
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