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publicationDate 2004-12-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber BR-0214863-A
titleOfInvention Process for the synthesis of chirally pure beta-amino alcohols
abstract "PROCESS FOR THE SYNTHESIS OF CHINESE PURE AMINO-ALCOHOLS". The invention relates to a process for preparing chirally pure β-amino acid S-enantiomers comprising the steps of: a) preparing an organometallic reagent from an alkyl halide of Formula (R) 2 -CH (CH2) 2 ~) ~ n ~) CH ~ 2 ~ X; b) adding the organometallic reagent to carbon dioxide to provide a carboxylic acid; c) activating the carboxylic acid with an acid chloride, phosphorus trichloride, acid anhydride, or thionyl chloride in the presence of a tertiary amine base; d) reacting the product of step c) with an S-4-benzyl-2-oxazolidinone alkali metal salt; e) treating the product of step d) with a strong non-nucleophilic base to form an enolate anion; f) attaching the enolate anion with 2,4,6-triisopropylbenzenesulfonyl azide to provide an azaz oxinolidinone; g) hydrolyzing oxazolidinone azide with an aqueous base to provide an acid β-azide; h) reducing the acid β-azide to the β-amino acid; and i) recrystallizing the β-amino acid from the chirally pure β-amino acid. Also provided is a process for preparing chirally pure β-amino-alcohol S-enantiomers further comprising the steps of reducing crude β-amino amino acid and recrystallizing β-amino alcohol for Chirally pure α-amino alcohol. Also provided is a process for preparing chirally pure N-sulfonyl? -Amino alcohol enantiomers further comprising the steps of sulfonylating? -Amino alcohol with 5-chloro-thiophene-2-sulfonyl halide; and recrystallizing to afford the chirally pure N-sulfonyl? -amino alcohols.
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