Efficient enantioselective addition reaction using an...

Details Efficient enantioselective addition reaction using an... Efficient enantioselective addition reaction using an...

C - Chemistry, Metallurgy

07

C

C07C 215/68 (2006.01) C07D 471/08 (2006.01) C07D 265/18 (2006.01)

Patent

CA 2289206

An efficient method for the preparation of key intermediate, in the synthesis of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one, a reverse transcriptase inhibitor is achieved using a chiral addition reaction to the 4-chloro-2- trifluoromethylketoaniline with an organozinc complex to give the desired alcohol. This instant method has broad applicability in the chiral addition to any prochiral ketone.

L'invention concerne un procédé efficace pour la préparation de produit intermédiaire clé, dans la synthèse de (-)-6-chloro-4-cyclopropyléthynyl-4-trifluorométhyl-1,4-dihydro-2H-3,1-benzoxazine-2-un, qui est un inhibiteur de transcriptase inverse. On utilise une réaction d'addition chirale à la 4-chloro-2-trifluorométhylcétoaniline, avec un complexe organate-zinc, pour obtenir l'alcool recherché. Ledit procédé est largement applicable dans l'addition chirale à toute cétone prochirale.

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