Preparation of bile acids and intermediates thereof

A method for preparing deoxycholic acid (DCA) or a pharmaceutically acceptable salt thereof:

• said method comprising
• (a) reacting 9α-hydroxyandrost-4-en-3,17-dione 1.0 with H2 under hydrogenation conditions to form compound 1.1
• (b) reacting compound 1.1 with acid to form compound 1.2
• (c) reacting compound 1.2 with a reducing agent to form compound 1.3 or a mixture of 1.3 and 1.4
• (d) reacting compound 1.3 with a two carbon olefination reagent under olefin forming conditions to form compound 1.5
• (e) converting compound 1.5 to a compound of formula 1.6 wherein P is a protecting group
• (f) reacting the compound of formula 1.6 with an alkylpropiolate of the formula CH≡CC(O)OR or an alkyl acrylate of the formula CH2═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 an alkyl, and the dashed line is a single or double bond;
• (g) reacting the compound of formula 1.7 with H2 under hydrogenation conditions to form a compound of formula 1.8 wherein P is a protecting group and R is alkyl
• (h) reacting the 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
• (i) reacting the compound of formula 1.9 with H2 under hydrogenation conditions to form a compound of formula 2.0 wherein P is a protecting group and R is alkyl
• (j) reacting the 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
• (k) exposing the compound of formula 2.1 to deprotection and hydrolysis conditions to form deoxycholic acid or a pharmaceutically acceptable salt thereof.