ChemicalBook CAS DataBase List Tibolone

Tibolone synthesis

12synthesis methods

Product Name:Tibolone
CAS Number:5630-53-5
Molecular formula:C21H28O2
Molecular Weight:312.45

15506-05-5 Synthesis

15506-05-5
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5630-53-5
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Yield:5630-53-5 78%

Reaction Conditions:

Stage #1: 3-Methoxy-7α-methyl-17α-aethinyl-17β-hydroxy-Δ^2,5(10)-19-norandrastadienwith ascorbic acid in ethanol at 20 - 30; for 1 h;Activated Carbon Darco G₆₀;
Stage #2: with hydrogenchloride in ethanol;water at 20 - 25;

Steps:

8 Example 8

Activated Carbon Darco G60 (3.90 g) was added to a degassed solution of compound (10A) and ascorbic acid (99%, 195 MG) in ethanol (96%, 658 G). The suspens. ion was stirred under nitrogen for one hour at 20-30 C and clarified by filtration. To the resulting clear solution, water (13. 3 ML) and hydrochloric acid (0. 1N, 29. 64G) were added, with stirring under nitrogen. The reaction was maintained at 20-25 C and monitored by HPLC; additional charges of hydrochloric acid were added as necessary until the reaction was complete. On completion, aqueous potassium acetate (0. 1M, 585 ML) WAS added to quench the reaction. The reaction mixture was then cooled to 0-5 C for 1 hour. The resulting suspension was filtered and the filter cake washed with water. The product (11) was dried under vacuum at 30-35 C to constant weight (yield: 78%).

References:

WO2004/78774,2004,A1 Location in patent:Page 41