90457-65-1

Basic information

• Product Name: 17R-Drospirenone
• Synonyms: 17R-Drospirenone;Drospirenone Related Compound A (15 mg) (17-Hydroxy-6beta,7beta:15beta,16beta-dimethylene-3-oxo-17beta-pregn-4-ene-21-carboxylic acid, gamma-lactone);[6R-(6α,7α,8β,9α,10β,13β,14α,15α,16α,17α)]-1,3',4',6,7,8,9,10,11,12,13,14,15,16,20,21-Hexadecahydro-10,13-diMethyl-spiro[17H-dicyclopropa[6,7:15,16]cyclopenta[a]phenanthrene-17,2'(5'H)-furan]-3,5'(2H)-dione;Drospirenone Related CoMpound A;17-epi-Drospirenone
• CAS NO: 90457-65-1
• Molecular Formula: C₂₄H₃₀O₃
• Molecular Weight: 366.4932
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 90457-65-1.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 17R-Drospirenone(CAS DataBase Reference)
• NIST Chemistry Reference: 17R-Drospirenone(90457-65-1)
• EPA Substance Registry System: 17R-Drospirenone(90457-65-1)

Safety Data

• Hazardous Substances Data: 90457-65-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 90457-65-1 differently. You can refer to the following data:
1. A derivative of Drospirenone (D689500) with a reversed configuration of the 17-spirolactone ring had no biological activity. Drospirenone impurity.
2. 17R-Drospirenone (Drospirenone EP Impurity E) is a derivative of Drospirenone (D689500) with a reversed configuration of the 17-spirolactone ring had no biological activity. Drospirenone impurity.

Upstream product

• 197721-70-3 5β-hydroxy-3-carbonyl-6β,7β,5β,16β-dimethylene-17α-pregna-21,17-carboxylactone 
• 1248589-68-5 C₂₆H₃₈O₅ 
• 82546-55-2 3β,5-dihydroxy-6β,7β;15β,16β-dimethylene-5β,17α-pregna-21,17-carbolactone 
• 67372-65-0 3β-hydorxy-15β,16β-methylene androst-5-ene-17-one 
• 1015063-83-8 C₂₅H₃₀O₅ 
• 82543-18-8 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol 
• 1030361-89-7 C₃₃H₆₀O₃Si₂ 
• 1030361-88-6 C₃₃H₆₀O₄Si₂ 
• 1030361-86-4 C₃₂H₅₆O₃Si₂ 
• 1030361-84-2 C₃₂H₅₈O₂Si₂ 
• 81721-23-5 15β,16β-methylenandrost-5-ene-3β,17β-diol 
• 1030362-02-7 C₂₅H₃₆O₆S 
• 1030361-99-9 C₂₄H₃₄O₄ 
• 1030361-97-7 C₃₆H₆₂O₄Si₂ 

Downstream Products

• 74220-07-8 Spirorenone 
• 90457-65-1 dihydrospirorenone 
• 932388-89-1 7β-chloromethyl-15β,16β-methylene-3-oxo-17β-pregn-4-ene-21,17-carbolactone 
• 932388-89-1 7β-chloromethyl-15β,16β-methylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone 

Relevant articles and documents

Synthetic method of drospirenone

The invention provides a synthetic method of drospirenone. Belong to organic synthesis field. A compound having the structure shown in the formula II is obtained, 17-bit hydroxyl group is oxidized to a carbonyl group under the action of a noble metal catalyst and a persulfate, and the hydroxyl group on the III-position propyl group is oxidized into an aldehyde group, and then a hydroxyl aldehyde condensation forms a five-membered carboxylic acid lactone ring to obtain a compound having the structure shown 17 α in the formula IV 3. The compound drospirenone with the structure shown I is obtained, most of the raw materials are cheap, the high-pressure catalytic hydrogenation and is omitted, and meanwhile, the yield can reach 77% under mild reaction conditions. Drospirenone with a purity 99.6%.

PROCESS FOR THE PREPARATION OF DROSPIRENONE

A process is described wherein, by employing 17a-(3-hydroxypropyl) -63,7β3;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (II) as starting product, in a single stage reaction there is obtained drospirenone, (I), whereby the reaction is achieved using gaseous oxygen as the stoichiometric oxidant in the presence of a catalytic system containing (i) TEMPO or a derivative thereof, (ii) a ferric salt (Fe3+) and (iii) NaCI. The product drospirenone is a known synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic action, that is useful for preparing pharmaceutical compositions with contraceptive action.

Process for the preparation of drospirenone

It is described a process for the preparation of Drospirenone, a synthetic steroid with progestogenic anti-mineralocorticoid and antiandrogenic activity having the formula 1 shown below, useful in the preparation of contraceptive pharmaceutical compositions, starting from 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstan-3β,5,17β-triol.