Dynamic thermodynamic resolution of N-methylpseudoephedrine α-bromo esters for asymmetric syntheses of α-hydroxy carboxylic acid derivatives

Tetrahedron

Volumn 59, Issue 14, 2003, Pages 2397-2401

  Nam, Jiyoun ^a   Lee, Sang Kuk ^a   Park, Yong Sun ^a  

^a Konkuk University   (South Korea)

Author keywords

Asymmetric syntheses; Chiral auxiliaries; Dynamic thermodynamic resolution; Nucleophilic substitution; hydroxy carboxylic acid

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; EPHEDRINE DERIVATIVE; METHYL 2 (4 ANISYLOXY) 4 PHENYLBUTANOATE; METHYL 2 (4 ANISYLOXY)BUTANOATE; METHYL 2 (4 ANISYLOXY)HEXANOATE; METHYL 2 (4 ANISYLOXY)PROPANOATE; N METHYLPSEUDOEPHEDRINE 2 BROMO 4 PHENYLBUTANOATE; N METHYLPSEUDOEPHEDRINE 2 BROMOBUTANOATE; N METHYLPSEUDOEPHEDRINE 2 BROMOHEXANOATE; N METHYLPSEUDOEPHEDRINE 2 BROMOPROPANOATE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DIASTEREOISOMER; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 0037474626     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00285-0     Document Type: Article

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19. Both (S,S)- and (R,R)-N-methylpseudoephedrine are commercially available and also can be easily prepared by N-methylation of pseudoephedrine with MeI and NaH.
20. 3N is attributed to the internal base on N-methylpseudoephedrine.
21. 1H NMR of authentic epimers prepared from commercially available compounds. Those of (αS)-3 and (αS)-4 were assigned by analogy to the formation of (αS)-1 and (αS)-2.
22. 3CN at room temperature gave no detectable epimerization.
23. (a) It has been confirmed that the dr of the precursor of 5 is retained during the methanolysis of the reaction mixture and isolation process to recover 5. (b) The absolute configuration of (R)-8 was assigned by comparison of CSP-HPLC retention time with the reported value in Ref. 3e. Those of (R)-5, (R)-6 and (R)-7 were assigned by analogy to the formation of (R)-8. In each case the minor (S)-enantiomer eluted more rapidly than the major (R)-enantiomer. See Section 4.
24. The maximum error on all er values, as derived from chiral stationary phase HPLC analysis, is ±1%.
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27. 1H NMR of reaction mixture.