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The synthesis of novel molecules is an essential aspect of the chemical industry, as it allows for the creation of new materials and substances with unique properties.
One such molecule that has garnered recent attention in the scientific community is (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine.
This molecule possesses unique structural features and potential pharmacological properties, making it an interesting subject for further study and synthesis.
The synthesis of (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine involves a multi-step process that requires careful attention to detail and manipulation.
The synthesis of this molecule is not a trivial task and requires a thorough understanding of organic synthesis, reaction mechanisms, and the use of specialized equipment.
The first step in the synthesis of (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine is the synthesis of the intermediate (1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol.
This molecule is synthesized by reacting 3,5-dimethyl-1,2-benzoxaborole with 3,3,3-trifluoropropionyl chloride in the presence of a Lewis acid catalyst, such as aluminum chloride.
The reaction is then treated with aqueous sodium hydroxide solution to hydrolyze the oxonium ion, resulting in the formation of the desired (1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol intermediate.
The next step in the synthesis of (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine is the reaction of the (1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol intermediate with 2-(4-fluorophenyl)acetaldehyde.
This reaction is carried out in the presence of a polar protic solvent, such as acetonitrile, and a base, such as sodium hydroxide.
The reaction is then treated with sodium periodate to oxidize the aldehyde group, resulting in the formation of the desired (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine.
The final step in the synthesis of (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine involves the protection of the hydroxyl group with a tert-butyl ester group.
This is achieved by treating the (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine with tert-butyl bromide in the presence of a Lewis acid catalyst, such as zinc chloride.
The resulting (2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morphinan-3-yl tert-butyl ester can then be purified and used as a starting material for further synthetic steps or as a final product for use in pharmaceutical or other applications.
In conclusion, the synthesis of (2