Some methods of preparing chenodeoxycholic acid are achieved by hydrogenation of C11 olefins. The key intermediate product in this process is compound (7). Nakada uses Fieser's synthetic method to dehydrate 3α, 7α-diacetyl-12α-hydroxy-5β-cholic acid in POCl3 in pyridine to form double bonds between C11 and C12, resulting in a critical intermediate production (7), the yield of 40% to 45%. Chen is reacted with hexamethylphosphoric triamide (HMPA) in potassium acetate via 3α, 7α-diacetyl-12-methanesulfonyloxy-5β-cholic acid methyl ester (8) to remove methanesulfonyloxy to give (7) a palladium-catalyzed hydrogenation reaction to yield the ester (9). And then hydrolyzed with methanol containing 10% NaOH to give chenodeoxycholic acid (Scheme 4) in a yield of 80%.
Wang Zhongqi, such as methyl ochidoxylate as raw material, three-dimensional selective synthesis of chenodeoxycholic acid. Zhang Fei, etc. on its basis to pig deoxycholic acid (10) as raw material synthesis of chenodeoxycholic acid, porcine deoxycholic acid by methyl esterification with p-toluenesulfonyl chloride reaction 3α, 6α-di-p-toluenesulfony (11), Oppenauer oxidation, 6,7-site dehydrogenation, epoxidation, catalytic hydrogenation, 3-position selective synthesis of chenodeoxycholic acid (1), total production the rate was 26% and the purity was 97.5% (Scheme 5).