Method for preparing cinacalcet intermediate R-(+)-1-(1-naphthyl)ethamine

A technology of ethylamine and naphthyl, applied in the field of preparation of cinacalcet intermediate R--1-ethylamine, can solve the problems of high production cost, high price of naproxen, large amount of toluene and dichloromethane, etc. , to achieve the effect of low cost

Active Publication Date: 2013-12-04
CHINA PHARM UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] (1) The post-processing operation is cumbersome
[0008] (2) Intermediates are not isolated, which is not conducive to quality control
[0009] (3) The resolution agent D-(+)-naproxen is expensive, resulting in high production costs
[0010] (4) The second-class solvents, toluene and methylene chloride, are used in large amounts, which is not conducive to environmental protection

Method used

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  • Method for preparing cinacalcet intermediate R-(+)-1-(1-naphthyl)ethamine
  • Method for preparing cinacalcet intermediate R-(+)-1-(1-naphthyl)ethamine
  • Method for preparing cinacalcet intermediate R-(+)-1-(1-naphthyl)ethamine

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Embodiment 1

[0024] Synthesis of N-(1-naphthylethyl)formamide (III)

[0025] Add 1-naphthyl ethyl ketone (50g, 0.29mol) and ammonium formate (148g, 2.35mol) into a 500ml three-necked flask, heat to reflux slowly, keep the internal temperature at 145-165°C for reflux and water separation for 8 hours, monitor by TLC after the reaction is complete , cooled to room temperature, added 300ml of dichloromethane to dissolve, poured into 300ml of water, extracted with dichloromethane, combined organic layers, washed with water, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated the filtrate to obtain off-white solid, petroleum Ether: ethyl acetate = 1:1 was dissolved into a white suspension, filtered by suction, washed with petroleum ether: ethyl acetate = 1:1 to obtain a white powdery solid, and dried to obtain 44.95 g of product III, with a yield of 76.7%. 1 H NMR (300MHz, CDCl 3 )δ8.18(1H,s,ArH),8.10(1H,d,J=8.1Hz,ArH),7.87(1H,d,J=7.8Hz,ArH),7.81(1H...

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Abstract

The invention relates to the field of drug synthesis, in particular to a method for preparing a cinacalcet intermediate R-(+)-1-(1-naphthyl)ethamine. The method is characterized in that D-tartaric acid which is low in price and easy to obtain is selected to replace D-(+)-naproxen to serve as a resolving agent, e.e. of an obtained product is up to 99.9%, and the method has the advantages of low cost, environmental friendliness and the like.

Description

technical field [0001] The invention relates to the field of drug synthesis. Specifically relates to the preparation method of cinacalcet intermediate R-(+)-1-(1-naphthyl)ethylamine. Background technique [0002] Optically active 1-(1-naphthyl)ethylamine is a resolving agent for racemic acid and an important pharmaceutical intermediate. (R)-(+)-1-(1-Naphthyl)ethylamine (I) is effective in the resolution of racemic monomenthyl phthalate to prepare L-menthol. The corresponding (S)-1-(1-naphthyl)ethylamine is a high-efficiency resolving agent for the resolution of amino acid acetylated derivatives. Meanwhile (R)-(+)-1-(1-naphthyl)ethylamine is an important intermediate in the synthesis of the second-generation calcimimetic cinacalcet for the treatment of hyperthyroidism. (R)-(+)-1-(1-naphthyl)ethylamine (I) structural formula is as follows: [0003] [0004] WO2008058235 discloses the preparation method of (R)-(+)-1-(1-naphthyl)ethylamine as follows: [0005] [0006...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/88C07C211/30
Inventor 徐云根王均伟朱启华包小波
Owner CHINA PHARM UNIV
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