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, applied in preparation, optically pure 1, can solve the problems of many steps, low efficiency, no ee value data and so on

Active Publication Date: 2010-11-03
ASTATECH CHENGDU BIOPHARM CORP
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

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 b

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
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Example Embodiment

Example 13 - Preparation of (tert-butyldimethylsilyloxy)-propanol

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

Example Embodiment

Example 23 - Preparation of (tert-butyldimethylsilyloxy)-propionaldehyde

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. The reaction was stirred for 3 hours, TLC detected that the reaction was complete, filtered through silica gel, dried and filtered over anhydrous magnesium sulfate and used directly for the next reaction.

Example Embodiment

Example 33 - Preparation of (tert-butyl-dimethylsilyloxy)-propionaldehyde

3-(tert-butyldimethylsilyloxy)-propanol (10 g, 52.5 mmol) was dissolved in a mixed solvent of 185 mml of dichloromethane (dried over 4A molecular sieves) and 75 mml of dimethyl sulfoxide (dried over 4A molecular sieves), and added 2-iodoylbenzoic acid (18 g, 64.3 mmol) was reacted at room temperature for 5 hours, and after monitoring the completion of the reaction by TLC, it was filtered through celite, washed with dichloromethane, and the organic phases were combined, washed with water, saturated brine, and 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 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 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. Optically pure dapoxetine mainly obtains the racemate through different synthetic routes and adopts the met...

Claims

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Application Information

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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
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