Regio- and stereospecific syntheses of syn- and anti-1,2- imidazolylpropylamines from the reaction of 1,1′-carbonyldiimidazole with syn- and anti-1,2-amino alcohols

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 5124-5127

  Mulvihill, Mark J ^a   Cesario, Cara ^a   Smith, Vanessa ^a   Beck, Patricia ^a   Nigro, Anthony ^a  

^a OSI PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CHEMICAL REACTIONS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

AMINO ALCOHOLS; STEREOSPECIFIC CONVERSION;

ALCOHOLS;

1,2 IMIDAZOLYLPROPYLAMINE DERIVATIVE; AMINOALCOHOL; CARBONYLDIIMIDAZOLE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINO ALCOHOLS; HISTAMINE; IMIDAZOLES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 3543002876     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049677l     Document Type: Article

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40. 1H NMR spectra. Also, direct comparison to the chemical shifts and coupling constants observed for N-methylpseudoephedrine and N-methylephedrine reveals that the carbinolic proton of the anti-amino alcohols is downfield with respect to the carbinolic proton of the syn-amino alcohols, a trend that was observed in the anti-amino alcohols (±)-14b,d,f and syn-amino alcohols (±)-14a,c,e, respectively,
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