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Generated: October 17, 2017

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Title:Preparation of bile acids and intermediates thereof
Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.
Inventor(s): Prasad; Achampeta Rathan (Hyderabad, IN), Swaringen, Jr.; Roy A. (Durham, NC), Reid; John Gregory (Niskayuma, NY), Moriarty; Robert M. (Michiana Shores, IN), Sahoo; Akhila Kumar (Bhubaneswar, IN)
Assignee: Kythera Biopharmaceuticals, Inc. (Calabasas, CA)
Filing Date:May 25, 2011
Application Number:13/115,889
Claims:1. A method for preparing deoxycholic acid (DCA) or a pharmaceutically acceptable salt thereof: ##STR00029## said method comprising (a) reacting compound 1.3 ##STR00030## with a two carbon olefination reagent under olefin forming conditions to form compound 1.5 ##STR00031## (b) converting compound 1.5 to a compound of formula 1.6 wherein P is a protecting group ##STR00032## (c) reacting a compound of formula 1.6 with an alkylpropiolate or an alkyl acrylate CH.sub.2.dbd.CHC(O)OR wherein R is alkyl in the presence of a Lewis acid to form a compound of formula 1.7 wherein P is a protecting group, R is a alkyl, and the dashed line ---- is a single or double bond; ##STR00033## (d) reacting a compound of formula 1.7 with H.sub.2 under hydrogenation conditions to form a compound of formula 1.8 wherein P is a protecting group and R is alkyl ##STR00034## (e) reacting compound of formula 1.8 with an oxidizing agent to form a compound of formula 1.9 wherein P is a protecting group and R is alkyl ##STR00035## (f) reacting a compound of formula 1.9 with H.sub.2 under hydrogenation conditions to form compound of formula 2.0 wherein P is a protecting group and R is alkyl ##STR00036## (g) reacting compound of formula 2.0 with a reducing agent to form a compound of formula 2.1 wherein P is a protecting group and R is alkyl ##STR00037## (h) exposing compound of formula 2.1 to deprotection and hydrolysis conditions to form deoxycholic acid.
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