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A method for preparing (1s, 2r, 3s, 4r)-2,3-o-isopropylidene-4-aminocyclopentane-1,2,3-triol

A technology of aminocyclopentane and isopropylidene, which is applied in the chemical industry, can solve the problems of non-recycling and increased production costs, and achieve the effects of increased yield, low price, and reduced costs

Active Publication Date: 2015-11-18
CHAMBROAD CHEM IND RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This route uses protected chiral amino acids as prosthetic groups to induce configuration, but it cannot be recycled, which increases production costs

Method used

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  • A method for preparing (1s, 2r, 3s, 4r)-2,3-o-isopropylidene-4-aminocyclopentane-1,2,3-triol
  • A method for preparing (1s, 2r, 3s, 4r)-2,3-o-isopropylidene-4-aminocyclopentane-1,2,3-triol
  • A method for preparing (1s, 2r, 3s, 4r)-2,3-o-isopropylidene-4-aminocyclopentane-1,2,3-triol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (1) Synthesis of R-ethyl mandelate

[0049]

[0050] Weigh 10.5g R-mandelic acid into a reaction bottle filled with 50ml of absolute ethanol, then slowly add 2ml of concentrated sulfuric acid along the wall, reflux at 80°C for 4 hours, remove the solvent by rotary evaporation, then add an appropriate amount of dichloromethane, and wash with water Twice, the organic layer was dried with anhydrous sodium sulfate, filtered and spin-dried to obtain 12 g of product, yield: 96.46%.

[0051] (2) Synthesis of compound VI

[0052]

[0053] Weigh 12g of potassium hydroxide and dissolve it in 40ml of anhydrous methanol at room temperature, pour 9g of hydroxylamine hydrochloride into a solution of 60ml of anhydrous methanol under nitrogen protection, a large amount of white solids are produced, filter, and the filtrate is cooled to 0 degrees; Measure 12g of R-methyl mandelate into the reaction flask, stir overnight at room temperature, remove the solvent by rotary evaporatio...

Embodiment 2

[0062]

[0063] For the specific preparation method, refer to Example 1.

Embodiment 3

[0065]

[0066] For the specific preparation method, refer to Example 1.

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Abstract

The invention provides a preparation method of (1S,2R,3S,4R)-2,3-O-isopropylidene-4-aminocyclopentyl-1,2,3-triol, which comprises the following steps: dissolving hydroxylamine derivative in a methanol-water mixed solvent, adding new-made sodium periodate and cyclopentadiene in an ice bath, reacting, and treating to obtain a compound V; and adding the compound V into N-methylmorpholinyl-N-oxynitride and tetrahydrofuran, oxidating with osmium tetroxide to obtain a compound IV, reacting the compound IV with 2,2-dimethoxypropane under the action of a catalyst to obtain a compound III, carrying out alkaline hydrolysis on the compound III to obtain a compound II, and reducing the compound II under the catalytic hydrogenation action of palladium on carbon to obtain the target product (1S,2R,3S,4R)-2,3-O-isopropylidene-4-aminocyclopentyl-1,2,3-triol. The method optimizes the technique, lowers the production cost, and enhances the reaction yield.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, in particular to a key intermediate for preparing ticagrelor-(1S,2R,3S,4R)-2,3-O-isopropylidene-4-aminocyclopentane-1,2 , 3-triol method. Background technique [0002] Since the results of ticagrelor (Brilinta) were first announced at the European Society of Cardiology (ESC) in 2009, the American Transcatheter Cardiovascular Therapy (TCT) Academic Annual Meeting and the American Heart Association (AHA) Annual Meeting have successively Some research results of this product are discussed. As a new oral antiplatelet drug, ticagrelor can reduce the incidence of cardiovascular diseases such as heart disease, and reduce the cardiovascular mortality in patients with acute coronary syndrome (ACS), so it has become the focus of much attention in the industry. [0003] (1S,2R,3S,4R)-2,3-O-Isopropylidene-4-aminocyclopentane-1,2,3-triol is an important intermediate of ticagrelor. The synthesis r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/44C07D261/20C07D498/08
CPCC07D261/20C07D317/44C07D498/08
Inventor 王军政张建林吴文雷孙智华
Owner CHAMBROAD CHEM IND RES INST CO LTD
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