147199-40-4Relevant articles and documents
Synthesis method of dapoxetine impurities
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, (2021/07/08)
The invention provides a synthesis method of dapoxetine impurities, which comprises the following synthesis steps of: reacting (S)-3-amino-3-phenyl propanol with Boc anhydride to obtain a compound B; reducing the compound B under the action of a reducing agent to obtain a dapoxetine impurity 1; reacting the impurity 1 with 1-fluoronaphthalene under the action of alkali to obtain an impurity 2; and reacting the impurity 2 with chloroformate to obtain an impurity 3. According to the synthesis method of the dapoxetine impurities, the three dapoxetine impurities can be obtained in sequence, the starting raw materials are wide in source, the cost is low, the synthesis steps are short, all the steps are conventional experiment operation, special reagents or toxic reagents do not need to be used, and the prepared dapoxetine impurity products are high in purity and do not need tedious purification operation. The synthesized three impurities are applied to dapoxetine hydrochloride quality control, are helpful for perfecting the quality standard of dapoxetine hydrochloride, and have important meanings for improving the quality of dapoxetine hydrochloride raw material medicines and preparations thereof and the medication safety.
Development of novel triazole based dendrimer supported spiroborate chiral catalysts for the reduction of (: E)-O-benzyl oxime: An enantioselective synthesis of (S)-dapoxetine
Anandhan, Ramasamy,Reddy, Mandapati Bhargava,Sasikumar, Murugesan
, p. 15052 - 15056 (2019/10/08)
Novel dendrimer supported spiroborate catalysts 2 and 3 have been synthesized using a click reaction as a key step. The catalytic efficiency of the catalysts have been verified with reduction of (E)-O-benzyl oxime 13 as a model substrate. Catalyst 3 was found to be better than catalyst 2 as the chemical yield and enantiomeric excess were significantly high with the former catalyst. Thus, catalyst 3 has been successfully used in the efficient synthesis of (S)-dapoxetine 14 with 94% ee and 46% overall yield in three steps. These catalysts could be easily recovered from the reaction solution by the solvent precipitation technique and could be reused five times without significant loss of activity and enantioselectivity.
Preparation method of dapoxetine hydrochloride impurities
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, (2018/06/15)
The invention discloses a preparation method of three impurities with similar structures for dapoxetine hydrochloride: (S)-3-(naphthalene-1-oxo)-1-phenylpropy-1-amine (compound II), (S)-N-methyl-3-(naphthalene-1-oxo)-1-phenylpropy-1-amine (compound III) and (S)-N,N-dimethyl-3-(naphthalene-2-oxo)-1-phenylpropy-1-amine (compound IV). The preparation method comprises the following steps: taking (S)-3-amino-3-phenylpropy-1-ol (VII) as a starting raw material; carrying out a multiple-step reaction such as amino protection, hydroxyl activation, substitution and amino deprotection to respectively obtain a compound II, a compound III and a compound IV as impurities of the dapoxetine hydrochloride. According to a preparation route, the starting raw materials are easy to obtain; reaction conditionsare mild and the selectivity is high; a sample with higher purity (98 percent or above) can be obtained according to a conventional post treatment method, can be used as a reference substance of the compound II, the compound III and the compound IV that are impurities of the dapoxetine hydrochloride and is used for quality control over synthesis research of the dapoxetine hydrochloride.
