Stereoselective method for synthesizing dolaphenine

C - Chemistry – Metallurgy – 07 – D

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C07D 277/28 (2006.01) C07C 209/40 (2006.01) C07C 211/42 (2006.01) C07C 213/00 (2006.01) C07D 207/335 (2006.01) C07D 213/38 (2006.01) C07D 233/61 (2006.01) C07D 239/26 (2006.01) C07D 307/52 (2006.01) C07D 333/20 (2006.01)

Patent

CA 2224121

The present invention relates to a method for the stereospecific synthesis of an enantiomer of a chiral amine, wherein the chiral amine has the formula: R1CH(NH2)R2. R1 and R2 are each independently selected from the group consisting of alkyl, aryl and heterocyclic and radicals. This method is particularly useful for stereospecifically synthesizing S-dolaphenine. The method involves contacting a chiral enantioner of norephedrine with borane, within an aprotic solvent to form a complex for stereospecifically reducing oximies. The complex is then contacted with an oxime, thereby stereospecifically reducing said oxime to form an enantiomer of a chiral amine.

La présente invention concerne un procédé de synthèse stéréospécifique d'un énantiomère d'une amine chirale ayant la formule R?1¿CH(NH¿2?)R?2¿. R?1¿ et R?2¿ sont choisis chacun indépendamment dans le groupe constitué de radicaux éthérocycliques, aryle et alkyle. Ce procédé est particulièrement utile pour la synthèse stéréospécifique de S-dolaphénine. Le procédé consiste à mettre en contact un énantiomère chiral de norephédrine avec un borane dans un solvant aprotique pour former un complexe afin d'effectuer une réduction stéréospécifique des oximes. Le complexe est ensuite mis en contact avec un oxime, pour effectuer la réduction stéréospécifique de l'oxime et former un énantiomère d'une amine chirale.

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