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Preparation method of (s)-N-ethyl-2-aminomethylpyrrolidine

A technology of aminomethylpyrrolidine and ethylpyrrolidine, which is applied in the field of synthesis of (s)-N-ethyl-2-aminomethylpyrrolidine, can solve unfavorable industrialized production, difficult reaction, L-co-ammonia The problem of high acid cost, to achieve the effect of less by-products, easy reaction route and high yield

Inactive Publication Date: 2020-05-15
BEIJING VENTUREPHARM BIOTECH
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AI Technical Summary

Problems solved by technology

[0008] However, due to the relatively high cost of L-proline and certain difficulties in the N,O-diethylation reaction, it is also unfavorable for industrial production

Method used

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  • Preparation method of (s)-N-ethyl-2-aminomethylpyrrolidine
  • Preparation method of (s)-N-ethyl-2-aminomethylpyrrolidine
  • Preparation method of (s)-N-ethyl-2-aminomethylpyrrolidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Preparation of 2-amino-5-hydroxypentanoic acid methyl ester

[0023] Using 2-amino-5-hydroxyvaleric acid as a raw material, the esterification reaction with methanol is used to obtain 2-amino-5-hydroxyvaleric acid methyl ester. Specifically, methanol is added to the raw material, the molar ratio of 2-amino-5-hydroxypentanoic acid and methanol is 1:1.5, 2-amino-5-hydroxypentanoic acid and concentrated H 2 SO 4 The mass ratio is 1:0.2, reflux stirring 3h, 2-amino-5-hydroxypentanoic acid methyl ester yield is 90%, and its reaction equation is as follows:

[0024]

Embodiment 2

[0025] Example 2 Preparation of 2-ethylamino-5-hydroxypentanoic acid methyl ester

[0026] Get 2-ethylamino-5-hydroxyvaleric acid methyl ester product 10.0 g among the embodiment 1 and bromoethane 10.4 g are mixed in DMF (100ml), in N 2 Add NaH in batches under protection, stir at room temperature for 4-5 h, rinse with water after the reaction, extract with ethyl acetate, and distill under reduced pressure to obtain 9.8 g of the product with a yield of 82%. The reaction equation is as follows:

[0027]

Embodiment 3

[0028] Example 3 Preparation of methyl 5-bromo-2-ethylaminovalerate

[0029] Take 8.0 g of the product of Example 2 and add it to carbon tetrachloride (50ml) solvent, stir, add 8.7 g of liquid bromine dropwise, stir at 60°C for 2 hours, cool, and remove the solvent by rotary evaporation. 2 Cl 2 Wash the residue with water, separate the liquids, and distill under reduced pressure if there are signs, and obtain the target product, methyl 5-bromo-2-ethylaminovalerate, with a mass of 7.0 g and a yield of 64%. Its reaction equation is as follows:

[0030]

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Abstract

The invention provides a preparation method of (s)-N-ethyl-2-aminomethylpyrrolidine. 2-amino-5-hydroxyvaleric acid used as a raw material undergoes esterification protection to obtain methyl 2-amino-5-hydroxypentanoate, N-ethylation is further achieved through bromoethane, and then the N-ethyl-2-aminomethylpyrrolidine is prepared through hydroxyl halogenation, substitution cyclization, ammonolysisand reduction six-step reaction. High-cost raw materials and an N,O-diethylation reaction are successfully avoided, and the method has the advantages of easiness in implementation of the above reaction route, few byproducts, high yield reaching 64.2%, and suitableness for industrialization.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and mainly relates to a synthesis method of (s)-N-ethyl-2-aminomethylpyrrolidine represented by formula I. [0002] [0003] Formula I. Background technique [0004] Levosulpiride and sultopride are both amide antipsychotic drugs. Levosulpiride mainly treats schizophrenia, and can also be used for intractable vomiting, peptic ulcer and dizziness and headache after traumatic brain injury. It has strong antipsychotic effect and Antiemetic effect; sultopride mainly acts on dopamine D2 receptors, is a dopamine receptor blocker, and its sedative effect is stronger than sulpiride. Among them, (s)-N-ethyl-2-aminomethylpyrrolidine is an important intermediate in the synthesis of such drugs, also known as (s)-N-ethyl-2-aminomethylpyrrolidine, and its molecular formula is C 7 h 16 N 2 , and can also be used in the synthesis of synthetic drugs for detoxification. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09C07D207/16
CPCC07B2200/07C07D207/09C07D207/16
Inventor 李恩民姬东方赵国磊
Owner BEIJING VENTUREPHARM BIOTECH
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