Method of synthesizing enantiopure mexiletine analogues and novel β-thiophenoxy and pyridyl ethers
OwnerMargarita Ortiz-Marciales, Kun Huang +3inventors
InventorsMargarita Ortiz-Marciales, Kun Huang, Viatcheslav Stepanenko, Melvin De Jesus, Wildeliz Correa
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Abstract
A practical and efficient procedure for the enantioselective synthesis of mexiletine analogues using 10% of a novel spiroborate ester as chirality transfer agent is presented. A variety of mexiletine analogues were prepared with excellent enantioselectivities (91-97% ee) in good yield from readily available starting materials. The developed methodology was also successfully applied for the synthesis of novel β-amino ethers containing thiophenyl and pyridyl fragments.
Claims33
A method of synthesizing enantiopure Mexiletine Analogues and Novel β-Thiophenoxy and Pyridyl ethers comprising:
- reducing an O-benzyl oxime having the formula I:
- where R is a substituted or unsubstituted, alkyl, aryl group;
- Y is an oxygen atom or a sulfur atom and Ar is an aryl, alkyl, Pyridyl group;
- wherein said reduction is done in the presence of a catalyst agent having the formula II:
- where, the R and R1 groups are equal or different;
- a hydrogen atom or a substituted or unsubstituted, aryl, alkyl, cycloalkyl or aralkyl;
- R2 and R 3 groups are different;
- a hydrogen atom or a substituted or unsubstituted, alkyl, aryl, aralkyl group;
- and the R4 group is a H or a cycloalkyl or aralkyl group;
- and wherein the substituents R, R1, R2, R3, and R4 groups are substantially non-reactive.
Dependencies are inferred from the claim text.