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A kind of resolution method of aminoalcohol

An aminoalcohol and pure aminoalcohol technology, applied in the field of compound preparation, can solve the problems of unsatisfactory yield and optical purity, limited industrial application and high manufacturing cost, and achieve easy industrial production, low production cost and less environmental pollution. Effect

Active Publication Date: 2017-05-17
ANHUI BIOCHEM UNITED PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] US5034394A discloses a kind of chiral resolution method of optically pure aminoalcohol (technical process sees figure 2 ), the method uses expensive tartrate dibenzoate as a chiral resolution reagent, and the resolution solvents are acetonitrile and methanol. These resolution solvents cannot be recovered and must be burned, which limits their industrial application
[0007] CA02591566A discloses a kind of chiral resolution method of optically pure amino alcohol (technical process sees image 3 ), the chiral resolution reagent of this method is tartaric acid, and the resolution solvent is methanol. This method solves the problems such as difficult solvent recovery and high manufacturing cost, but there are defects such as yield and optical purity are not ideal enough

Method used

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  • A kind of resolution method of aminoalcohol
  • A kind of resolution method of aminoalcohol
  • A kind of resolution method of aminoalcohol

Examples

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Effect test

Embodiment 1

[0033] Example 1 Preparation of Optically Pure Amino Alcohol D-tartrate (3) and Optically Pure Amino Alcohol Hydrochloride (4)

[0034] The preparation method of the present embodiment optically pure amino alcohol D-tartrate (3) and optically pure amino alcohol hydrochloride (4) comprises the following steps:

[0035] 1) Dissolve 113 grams of racemic aminoalcohol (±)-1 and 75 grams of D-tartaric acid in 500 milliliters of methanol, and slowly add 42 milliliters of concentrated hydrochloric acid with a concentration of 37% under ice-water cooling; Continue stirring for 20 hours at room temperature; filter, wash the filter cake with methanol at 4°C, and dry to obtain 128 grams of (1R,4S)-amino alcohol D-tartrate crude product with an optical purity of 95.6% ee; 1R, 4S)-aminoalcohol D-tartrate crude product was recrystallized with 500 ml of methanol to obtain 122 g of (1R, 4S)-aminoalcohol D-tartrate (3), 99.7% ee; MS: 114 (MH + );

[0036] 2) Spin-dry the filtrate collected ...

Embodiment 2

[0039] Example 2 Preparation of Optically Pure Amino Alcohol L-Tartrate (5) and Optically Pure Amino Alcohol Hydrochloride (6)

[0040] The preparation method of optically pure amino alcohol L-tartrate (5) and optically pure amino alcohol hydrochloride (6) of the present embodiment comprises the following steps:

[0041] 1) Dissolve 113 grams of racemic amino alcohol (±)-1 and 75 grams of L-tartaric acid in 500 milliliters of methanol, and slowly add 42 milliliters of concentrated hydrochloric acid with a concentration of 37% under ice-water cooling; Continue stirring for 20 hours at room temperature; filter, wash the filter cake with methanol at 4°C, and dry to obtain 129 grams of (1S, 4R)-amino alcohol L-tartrate crude product with an optical purity of 95.3% ee; 1S, 4R)-amino alcohol L-tartrate crude product was recrystallized with 500 milliliters of methanol to obtain 121 grams of (1S, 4R)-amino alcohol L-tartrate (5), 99.6% ee; MS: 114 (MH + );

[0042]2) Spin-dry the ...

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Abstract

The invention belongs to the technical field of compound preparation, and in particular relates to an amino alcohol resolution method. The invention can realize acquisition of optically pure amino alcohol tartrate and optically pure amino alcohol hydrochloride by one resolution, and has the advanategs of high process yield, high optical purity and stable quality of the prepared products, little environmental pollution, low production cost and easiness for industrialization; and the prepared optically pure aminoalcohol D-tartrate salt (3) and optically pure aminoalcohol hydrochloride (6) can be directly used for the preparation of Abacavir and Carbovir without desalination.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and in particular relates to a resolution method of amino alcohol. Background technique [0002] Optically pure amino alcohol (1) is a key intermediate for the preparation of anti-AIDS drugs such as abacavir (Abacavir, EP434450) and carbavir (Carbovir, JOC1995, 60, 4602-16.). [0003] [0004] There are more than a dozen known asymmetric synthetic routes for optically pure amino alcohol (1), but all of them have defects such as lengthy synthetic routes, harsh reaction conditions, difficult availability of raw materials, and high manufacturing costs. [0005] Racemic amino alcohol (±)-1 can be prepared from racemic compound (±)-2 through protection (WO2005075426A), reduction (WO2006040625A), deprotection (EP0878548A) reaction steps (see process flow figure 1 ); and then perform chiral resolution on the racemic amino alcohol (±)-1 to obtain optically pure amino alcohol. [0006] U...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/10C07C215/42
Inventor 岳祥军钟晓锋田磊王志邦
Owner ANHUI BIOCHEM UNITED PHARMA CO LTD