1384968-41-5

Upstream product

• 136918-14-4 phthalimide 
• 908291-72-5 (R)-(-)-3-(1-naphthalenyloxy)-1-phenyl-1-propanol 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 103548-16-9 (R)-3-phenyl-1,3-dihydroxypropane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 90-15-3 α-naphthol 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 85-44-9 phthalic anhydride 

Downstream Products

• 147199-40-4 Didesmethyldapoxetine 
• 1404234-03-2 (S)-tert-butyl(3-(naphthalen-1-yloxy)-1-phenylpropyl)carbamate 

Relevant academic research and scientific papers

Simple and efficient synthesis of (S)-dapoxetine

A refinement in the synthetic strategy for (S)-dapoxetine 1 is described. The key features of synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and regioselective reductive ring opening of a 2,3-epoxy alcohol to elaborate the hydroxy-bearing stereogenic center at benzylic position; (b) regioselective functionalization of 1-naphthol and amine functionality through Mitsunobu procedures; and (c) Eschweiler-Clarke reductive methylation condition to access the target molecule.

Preparation method of dapoxetine hydrochloride impurities

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.