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Optical pure 1,3-alkamine compound as well as preparation method and application thereof in preparing Dapoxetine and analogues thereof

A technology of amino alcohols and compounds, which is applied in the preparation of amino hydroxyl compounds, organic compounds, carbamic acid derivatives, etc., which can solve problems such as many steps, low efficiency, and no ee value data

Active Publication Date: 2011-12-28
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these splitting methods are inefficient and the defects of large waste still exist
There are also some studies on the synthesis of (S)-3-amino-3-phenylpropanol using asymmetric synthesis methods, such as L-diethyl tartrate (Tetrahedron, 2009, 65, 2605-2609) or 1,4-diol (US 6207862) as a raw material, and eventually optically active 1,3-aminoalcohols can be synthesized, but the reaction is complicated, there are many steps, the total yield is low, and there is no ee value data
Taken together, the current methods for synthesizing (S)-3-amino-3-phenylpropanol are not satisfactory, either with high cost, large waste, or insufficient optical purity, and it is necessary to further develop economical and applicable routes

Method used

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  • Optical pure 1,3-alkamine compound as well as preparation method and application thereof in preparing Dapoxetine and analogues thereof
  • Optical pure 1,3-alkamine compound as well as preparation method and application thereof in preparing Dapoxetine and analogues thereof
  • Optical pure 1,3-alkamine compound as well as preparation method and application thereof in preparing Dapoxetine and analogues thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0198] The preparation of embodiment 13-(tert-butyldimethylsiloxy)-propanol

[0199] 1,3-propanediol (40g, 526mmol), imidazole (43g, 632mmol) is dissolved in the mixed solvent of dichloromethane and N, N-dimethylformamide (400ml, V DCM :V DMF =3:1), after cooling to -18°C, tert-butyldimethylsilyl chloride (79.4g, 526mmol) dissolved in 200ml of dichloromethane was slowly added dropwise to the above solution. After the reaction was completed, it was successively washed with water and saturated brine, and dried over anhydrous magnesium sulfate. Concentrate under reduced pressure to evaporate dichloromethane, and then distill under reduced pressure to obtain 80 g of the product with a yield of 80%.

Embodiment 23

[0200] Preparation of Example 23-(tert-butyldimethylsilyloxy)-propanal

[0201] 3-(tert-butyldimethylsilyloxy)-propanol (4g, 21mmol) was dissolved in 50ml of dichloromethane (dried over 4A molecular sieves), and pyridinium chlorochromate (5.4g, 25mmol) was added in batches, at room temperature Stir the reaction for 3 hours, TLC detects that the reaction is complete, filter through silica gel, dry and filter over anhydrous magnesium sulfate, and use it directly for the next reaction.

Embodiment 33

[0202] Example 33 - Preparation of (tert-butyl-dimethylsiloxy)-propanal

[0203] 3-(tert-butyldimethylsilyloxy)-propanol (10 g, 52.5 mmol) was dissolved in a mixed solvent of 185 mml dichloromethane (dried over 4A molecular sieves) and 75 mml dimethyl sulfoxide (dried over 4A molecular sieves), and added 2-iodanoylbenzoic acid (18g, 64.3mmol), after reacting at room temperature for 5 hours, TLC monitored that the reaction was complete, filtered it with diatomaceous earth, washed it with dichloromethane, combined the organic phases, washed them successively with water, washed them with saturated brine, and washed them with anhydrous sulfuric acid. The magnesium was dried and filtered and used directly for the next reaction.

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Abstract

The invention specifically relates to an optical pure 1,3-alkamine compound as well as a preparation method and application thereof in preparing corresponding optical pure 1,3-alkamine and further preparing Dapoxetine and analogues thereof, belonging to the technical field of organic chemistry. The 1,3-alkamine compound is as shown in a formula I.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and particularly relates to optically pure 1,3-aminoalcohol compounds, a preparation method and an application in preparing dapoxetine and its analogs. Background technique [0002] Dapoxetine ((S)-(+)-N, N-Dimethyl-3-(1-naphthyloxy)-1-phenylpropylamine, 1) was originally an antidepressant developed by Eli Lilly Company in 1992. It is a A selective serotonin reuptake inhibitor (SSRI). February 2009 as a drug for the treatment of male premature ejaculation (PE) (Prilig TM ) first launched in Finland and Sweden, which is the world's first oral treatment for this indication. It was listed as one of the five most promising drugs already on the market or under approval by Thomson Reuters (Thomson Reuters) quarterly report on major progress in global drug development in the first quarter of 2009. [0003] [0004] Optically pure dapoxetine mainly obtains the racemate through different s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C07C217/48C07C213/06C07C213/08C07C215/28C07C213/00C07C213/02C07C309/73C07C303/28C07C269/04C07C271/16C07D213/40
CPCY02P20/55
Inventor 谢义鹏郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP