ChemicalBook CAS DataBase List Dienogestrel

Dienogestrel synthesis

9synthesis methods

Product Name:Dienogestrel
CAS Number:65928-58-7
Molecular formula:C20H25NO2
Molecular Weight:311.43

Dienogest is an orally active synthetic progesterone (or progestin). It is available for use as an oral contraceptive in combination with ethinylestradiol. It has antiandrogenic activity and as a result can improve androgenic symptoms. It is a non-ethinylated progestin which is structurally related to testosterone. Dienogest given in isolation is available for the treatment of endometriosis under the trade name Visanne.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

Liang, Yong; Chen, Bo; Wang, Shaojie. Synthesis of dienogest. Shenyang Yaoke Daxue Xuebao. Volume 28. Issue 10. Pages 788-790. Journal. (2011).

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65928-58-7
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Yield:65928-58-7 99.9 %Chromat.

Reaction Conditions:

with perchloric acid in water;acetonitrile at 20 - 30; for 1 h;Reagent/catalyst;Solvent;

Steps:

3 Preparation of Crude Dienogest
The compound (100 g) of example-1 in acetonitrile (600 mL) was cooled to 0-5° C. and 70% perchloric acid (150 mL) was added and stirred for one hour at 20-30° C.
After completion of reaction, water (1500 mL) was added and solid was filtered to obtain crude product. (HPLC data: Dienogest-99.55%, diene impurity-0.125%). Purification of Crude Dienogest a) Wet solid from example-2 was charcoalised in dimethylformamide (400 mL) at 45-50° C. for one hour, filtered, washed with dimethylformamide (100 ml) and to the combined filtrate water (200 ml) was added. Reaction mass stirred for 2 hours at 0-5° C. Solid was filtered and dried under reduced pressure at 40-45° C. to give 66 g crude dienogest. (HPLC data: Dienogest - 99.79%, Diene impurity-0.02%).b) Dienogest (25 g) from example 3(a) was taken in dimethylformamide (125 mL) and heated to 40-50° C., filtered, washed with dimethylformamide (25 ml) and to the combined filtrate water (37.5 ml) was added to precipitate the product, cooled to 0 to 5° C. and stirred for 2 hours. Solid obtained was filtered, washed with water and dried under vacuum at 40-45° C. to give 23 g of Dienogest.(HPLC data: Dienogest - 99.9%, Diene impurity - 0.02%).

References:

LUPIN LIMITED;Tambe, Suhas Ganpat;Kirange, Bhushan Bhanudas;Singh, Gurvinder Pal;Ray, Purna Chandra US2013/41166, 2013, A1 Location in patent:Paragraph 0040