Patent ID: 8338628

Claim:
A method for producing 6α-ethylchenodeoxycholic acid (6-ECDCA) from chenodeoxycholic acid (CDCA) comprising the following steps: (i) oxidizing CDCA with pyridinium chlorochromate (PCC) to produce 5β-cholanicacid-3α-ol-7-one (ii) contacting a solution of 5β-cholanicacid-3α-ol-7-one with (a) 3,4-dihydro-2H-pyran and (b) p-toluenesulfonic acid to result 3α-tetrahydropyranyloxy-7-keto-5β-cholan-24-oic acid; (iii) contacting a solution of 3α-tetrahydropyranyloxy-7-keto-5β-cholan-24-oic acid with ethyl iodine to produce 3α-tetrahydropyranyloxy-6α-ethyl-7-keto-5β-cholan-24-oic acid; (iv) contacting 3α-tetrahydropyranyloxy-6α-ethyl-7-keto-5β-cholan-24-oic acid with pyridinium p-toluenesulfonate (PPTS) to result 3α-hydroxy-6α-ethyl-7-keto-5β-cholan-24-oic acid; and (v) reducing 3α-hydroxy-6α-ethyl-7-keto-5β-cholan-24-oic acid with NaBH 4 to produce 6-ECDCA