A concise asymmetric synthesis of torcetrapib

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 6290-6293

  Guinó, Meritxell ^a   Pim, Huat Phua ^a   Caille, Jean Claude ^b   King, Kuok Hii ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Z I la Croix Cadeau   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; ENANTIOSELECTIVITY; REACTION KINETICS;

AZA-MICHAEL REACTION; TORCETRAPIB;

DRUG PRODUCTS;

TORCETRAPIB;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REDUCTION; TEMPERATURE;

AMINO ACIDS; CARBAMATES; CATALYSIS; CHEMISTRY, ORGANIC; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM; TIME FACTORS;

EID: 34547630925     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071031g     Document Type: Article

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15. The process was replicated three times using various samples of 2 with enantiomeric excesses between 60 and 89%. On every occasion, samples recovered from the mother liquor were found to possess ee values of ≥95%. See Experimental Section for a representative procedure.
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18. Melting point recorded for a "solvent-free sample" was reported to be 142.3-142.4°C (ref 7b).
19. Resulting from the dimerization of the reactive benzyl bromide, giving a stilbene byproduct (ArCH=CHAr). This was reported previously in ref 7b.
20. In the original reports (ref 7), the base was added in two portions. Torcetrapib was obtained as a monoethanolate in 73% yield.
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