ChemicalBook CAS DataBase List methyl 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oate

methyl 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oate synthesis

7synthesis methods

Product Name:methyl 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oate
CAS Number:14772-99-7
Molecular formula:C25H40O5
Molecular Weight:420.58

1448-36-8 Synthesis

1448-36-8
156 suppliers
$5.00/100mg

methyl 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oate

14772-99-7
15 suppliers
inquiry

Yield:14772-99-7 98%

Reaction Conditions:

with Ag₂CO₃ on Celite in toluene;Reflux;Inert atmosphere;

Steps:

General procedure for the oxidation of the 3-hydroxyl group

To a solution of 1a (4.22 g, 10.0 mmol) in 200 mL toluene, freshly made Ag2CO3 on Celite4 (50% wt, 12.1 g, 22.0 mmol) was added in portions. Occasionally the suspension of Ag2CO3 on Celite had to be prerefluxed for 0.5 h to be activated and completely dehydrated. The suspension was refluxed and the water was removed by a Dean-Stark apparatus. The reaction was monitored by TLC until the starting material was consumed. The mixture was filtered to remove the solid, and the filtrate was concentrated in vacuo to provide a yellowish solid (2a, 4.1 g, 98% yield) with over 95% purity. Further purification was done by flash chromatography with eluent EA/Hex =1/2.

References:

Li, Qingjiang;Tochtrop, Gregory P. [Tetrahedron Letters,2011,vol. 52,# 32,p. 4137 - 4139] Location in patent:supporting information; experimental part