ChemicalBook CAS DataBase List 16,17-Epoxypregnenolone

16,17-Epoxypregnenolone synthesis

5synthesis methods

Product Name:16,17-Epoxypregnenolone
CAS Number:974-23-2
Molecular formula:C21H30O3
Molecular Weight:330.47

16α,17α-Epoxypregnenolone can be prepared by oxidation, hydrolysis, elimination and epoxidation of diosgenin.

979-02-2
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974-23-2
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$116.00/10g

Yield: 97%

Reaction Conditions:

with sodium hydroxide;urea hydrogen peroxide adduct in methanol;water at 5; for 72 h;

Steps:

1
16-Dehydropregnenolone acetate (35 g) is suspended in methanol (500 ml). The solution is treated, after cooling to 500° C. with 4N NaOH (8.9 gm in 50 ml H2O) followed by immediately with hydrogen peroxide-urea adduct (UHP, 18 g.). The mixture is then stored in the refrigerator at 5° C. for 72 hr. The reaction mixture is shaken intermittently. The reaction mixture is poured into 500 ml of ice water. The product is isolated by centrifugation after wash up with water till neutrality to pH paper. The product is dried (63.0 g, 97%) M.P. 187-90 (187-90°). [0029] 1H-NMR (CDCl3): δ 5.3 (m, 1H, olefinic proton), 3.67 (s, 1H, C16-H), 3.5 (m, 1H, C3-H), 2.0 (s, 3H, CH3CO); 1.2 and 1.0 (2s, 3H each, C18Me, C19Me).

References:

COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH US2004/186306, 2004, A1 Location in patent:Page 4

1162-53-4 Synthesis