Production of chirally pure amino alcohol intermediates,...

Details Production of chirally pure amino alcohol intermediates,... Production of chirally pure amino alcohol intermediates,...

C - Chemistry, Metallurgy

07

C

C07C 213/02 (2006.01) C07C 215/08 (2006.01) C07D 333/34 (2006.01)

Patent

CA 2649396

A method of selectively preparing a chiral 2S-amino alcohol useful in preparation of an amide sulfonated or acylated with alkyl, substituted aryl or substituted heteroaryl is described. The method involves reacting a di-tert-butyl diazene-l,2-dicarboxylate with a (4S)-4-benzyl-3-[(S)-trifluoromethyl - alkyl substituted alkanoyl]-l,3-oxazolidin-2-one to afford a di-tert-butyl 1-(1S,2S)-([(4S)- 4-benzyl-2-oxo-l ,3-oxazolidine-3-yl]-carbonyl}-trifluoromethyl- alkyl substituted alkyl)hydrazine-l,2-dicarboxylate. This dicarboxylate is then reduced to yield di- tert-butyl l-(lS,2S)-[trifluoromethyl-alkyl substituted alkyl]hydrazine-l- (hydroxymethyl)-l,2-dicarboxylate. The resulting product is deblocked with an acid to yield the acid addition salt of (2S,3S)-trifluoro-hydrazino-methyl alkan-1-ol. The acid addition salt of (2S,3S)-trifluor-2-hydrazino-methyl alkan-1-ol is hydrogenated in the presence of a suitable metal catalyst to yield the amino alcohol (2S,3S)-2- amino-trifluoro ~ methyl alkan-1-ol HCl.

Procédé de préparation sélective d'un (2S)-aminoalcool chiral utile dans la préparation d'un amide sulfoné ou acylé avec un alkyle, un aryle substitué ou un hétéroaryle substitué. Le procédé consiste à faire réagir un diazène-1,2-dicarboxylate de di-tert-butyle avec une (4S)-4-benzyl-3-[(S)-trifluorométhyl(alcanoyl substitué par un alkyle]-1,3-oxazolidin-2-one pour produire un 1-(1S,2S)-([(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}trifluorométhyl(alkyl substitué par un alkyle)hydrazine-1,2-dicarboxylate de di-tert-butyle. On effectue ensuite la réduction de ce dicarboxylate pour produire un 1-(1S,2S)-[trifluorométhyl(alkyl substitué par un alkyle)]hydrazine-1-(hydroxyméthyl)-1,2-dicarboxylate de di-tert-butyle. On débloque le produit résultant avec un acide pour produire le sel d'addition d'acide du (2S,3S)-trifluorohydrazinométhylalcan-1-ol. Le sel d'addition d'acide du (2S,3S)-trifluoro-2-hydrazinométhylalcan-1-ol est hydrogéné en présence d'un catalyseur en métal approprié pour produire l'aminoalcool (2S,3S)-2-aminotrifluorométhylalcan-1-ol HCl.

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