Synthesis of a histamine H 3 receptor antagonist - Manipulation of hydroxyproline stereochemistry, desymmetrization of homopiperazine, and nonextractive sodium triacetoxyborohydride reaction workup

Journal of Organic Chemistry

Volumn 75, Issue 13, 2010, Pages 4463-4471

  Pippel, Daniel J ^a   Young, Lana K ^a   Letavic, Michael A ^a   Ly, Kiev S ^a   Naderi, Bita ^a   Soyode Johnson, Aki ^a   Stocking, Emily M ^a   Carruthers, Nicholas I ^a   Mani, Neelakandha S ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; COST-OF-GOODS; DESYM-METRIZATION; L-PROLINE; MITSUNOBU REACTIONS; NATURALLY OCCURRING; RECEPTOR ANTAGONISTS; ROUTE SELECTION; SECOND GENERATION; SODIUM TRIACETOXYBOROHYDRIDE; STEREOGENIC CENTERS; WATER SOLUBILITIES;

SODIUM; STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

1 [2 (4 CYCLOBUTYL [1,4]DIAZEPANE 1 CARBONYL) 4 (3 FLUORO PHENOXY) PYRROLIDIN 1 YL] ETHANONE; BORANE DERIVATIVE; HISTAMINE H3 RECEPTOR ANTAGONIST; HYDROXYPROLINE; LACTONE; N BOC HOMOPIPERAZINE; PIPERAZINE DERIVATIVE; PROLINE DERIVATIVE; SODIUM TRIACETOXYBOROHYDRIDE; TRANS 4 HYDROXY LEVO PROLINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DESYMMETRIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MITSUNOBU REACTION; SOLUBILITY; STEREOCHEMISTRY;

AZEPINES; BOROHYDRIDES; CHROMATOGRAPHY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HISTAMINE H3 ANTAGONISTS; HYDROXYPROLINE; MAGNETIC RESONANCE SPECTROSCOPY; PYRROLIDINES; SODIUM; SOLUBILITY; SOLVENTS; STEREOISOMERISM; TEMPERATURE;

EID: 77954104443     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100629z     Document Type: Article

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