File:Oxandrolones synthesis.svg

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Original file(SVG file, nominally 548 × 356 pixels, file size: 31 KB)

Summary

Description
English: Counsell/Pappo synthesis of Oxandrolone
Date
Source

Recreated by Krishnavedala using reference:

Cabaj, John E.; Kairys, David; Benson, Thomas R. (2007). "Development of a Commercial Process to Produce Oxandrolone". Organic Process Research and Development 11 (3): 378–388. DOI:10.1021/op060231b.
Author Krishnavedala
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Source code
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SVG code

\documentclass[12pt,border=3pt,tikz,class=scrartcl,multi=false]{standalone}
\usepackage{times}
\usepackage[T1]{fontenc}
\usepackage[latin1]{inputenc}
\usepackage{mathtools,amssymb}
\usepackage{pgfplots}
\pgfplotsset{compat=1.12}
\usetikzlibrary{positioning,calc,arrows,fit,backgrounds,decorations.text,shapes}
 
\usepackage{chemfig,chemmacros}
\renewcommand*{\familydefault}{\sfdefault}
\renewcommand*\printatom[1]{\ensuremath{\mathsf{#1} } }
\setatomsep{1.7em}
\setdoublesep{.6ex}
\setarrowdefault{,1,ultra thick}
\setbondstyle{very thick,cap=but}
\definesubmol\nobond{-[,0.2,,,draw=none]}
 
\pagestyle{empty}
\thispagestyle{empty}
\begin{document}
\renewcommand{\baselinestretch}{.5}
\schemestart[][west]
    \chemfig{O=[:30]
    *6(--(<:[6]H)
    	*6(---
        	*6(-
            	*5(---(<:[::-20])(<[::-80]OH)-(<[2]))
             ----)
          --(<[2]))
     ----)
     }
     \arrow{->[\parbox{2.8cm}{1) \ch{Br2},\ch{NaOAc}\\\ch{AcOH}, rt}][\parbox{2.8cm}{2) \ch{LiCl},\ch{Li2CO3}\\DMF, reflux}]}[,2]
     \chemfig{O=[:30]
    *6(--(<:[6]H)
    	*6(---
        	*6(-
            	*5(---(<:[::-20])(<[::-80]OH)-(<[2]))
             ----)
          --(<[2]))
     --=-)
     }
     \arrow{->[*0\parbox{2.5cm}{\ch{OsO4}/\ch{Pb(OAc)4}\\\ch{AcOH},\ch{H2O}, rt}]}[-90]
     \chemfig{HO-[:30](=[:-30]O)-[2]-[::-60]
    	*6((<:[6]H)---
        	*6(-
            	*5(---(<:[::-20])(<[::-80]OH)-(<[2]))
             ----)
          --(<[2])(-[:150](=[::60]O)-[::-60]H)-)
     }
     \arrow{->[\ch{NaBH4},\ch{NaOH}][rt]}[180,2]
     \chemfig{O=[:30]
    *6(--(<:[6]H)
    	*6(---
        	*6(-
            	*5(---(<:[::-20])(<[::-80]OH)-(<[2]))
             ----)
          --(<[2]))
     ---O-)
     }
\schemestop
\end{document}

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Public domain This image of a simple structural formula is ineligible for copyright and therefore in the public domain, because it consists entirely of information that is common property and contains no original authorship.

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2 November 2014

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Date/TimeThumbnailDimensionsUserComment
current21:37, 11 April 2015Thumbnail for version as of 21:37, 11 April 2015548 × 356 (31 KB)Krishnavedalaupdated source-code and better conversion using dvisvgm
13:27, 8 November 2014Thumbnail for version as of 13:27, 8 November 2014591 × 412 (59 KB)Krishnavedalafixed reagent and structures according to reference
18:50, 2 November 2014Thumbnail for version as of 18:50, 2 November 2014591 × 412 (65 KB)KrishnavedalaUser created page with UploadWizard
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