90457-65-1

Usage

Uses

Used in Pharmaceutical Industry:
17R-Drospirenone is used as a pharmaceutical impurity for the purpose of quality control and assurance in the manufacturing process of Drospirenone. Its presence is monitored and controlled to ensure the safety, efficacy, and purity of the final product.

Upstream product

• 1015063-83-8 C₂₅H₃₀O₅ 
• 863329-70-8 6β,7β;15β,16β-dimethylene-5β-hydroxy-3-oxo-17α-pregn-21,17-carbolactol 
• 863329-71-9 6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4-en-21,17-carbolactol 
• 1104734-51-1 17α-[3-(trimethylsilanyloxy)propyl]-6β,7β,15β,16β-dimethylen-5β-androstane-3β,5,17β-triol 
• 1104734-52-2 17α-[3-(tert-butyldimethylsilanyloxy)propyl]-6β,7β,15β,16β-dimethylen-5β-androstane-3β,5,17β-triol 
• 1104734-54-4 17α-(2-[1,3]dioxolan-2-ylethyl)-6β,7β,15β,16β-dimethylen-5β-androstane-3β,5,17β-triol 
• 1104734-60-2 17α-(3,3-dimethoxypropyl)-6β,7β,15β,16β-dimethylen-androst-4-en17β-ol-3-one 
• 1104734-57-7 17α-[3-(tert-butyl-dimethylsilanyloxy)propyl]-6β,7β,15β,16β-dimethylenandrost-4-en-17β-ol-3-one 
• 67-64-1 acetone 
• 1248589-68-5 C₂₆H₃₈O₅ 
• 1774-47-6 trimethylsulfoxonium iodide 
• 67372-69-4 15β,16β-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone 
• 67372-65-0 3β-hydorxy-15β,16β-methylene androst-5-ene-17-one 
• 82543-18-8 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol 

Downstream Products

• 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 
• 74220-07-8 Spirorenone 

Relevant academic research and scientific papers

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%.

A drospirenone and intermediate preparation method (by machine translation)

The invention discloses a drospirenone and intermediate preparation method. Preparation method of this invention comprises the following steps: in the solvent, the compound 3 with hydrogen peroxide oxidation reaction shown below, to obtain compound 4 can be. Preparation method of this invention does not use a heavy metal reagent, reduces the toxicity of the preparation process, the use of the reagent are all conventional reagent, low cost, and is favorable for industrial large-scale production. (by machine translation)

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

A process is disclosed wherein, using either 17a-(3-hydroxypropyl)-6p,7p;15p,16p- dimethylene-5p-androstane-3p,5,17p-triol (II) or 3β,5^?Ι^κ^-6β,7β;15β,16β- dimethylene-5β,17α-pregnane-21,17-carbolactone (III) as starting material, through a single-step reaction it is obtained drospirenone (I), a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic activity, useful for preparing pharmaceutical compositions with contraceptive action.

Stereospecific synthesis of drospirenone

A procedure for the stereospecific synthesis of drospirenone has been developed. The key steps included the stereospecific reduction of the C 7-tertiary alcohol with ZnI2/Et3SiH, a novel mild and stereospecific tertiary alcohol reduction system, and the tandem oxidation/cyclopropanation reactions. Copyright

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.

Process for the Preparation of Drospirenone

A process is described, comprising the oxidation of 17α-(3-hydroxypropyl)-6β,7β,15β,16β-dimethylen-5β-androstan-3β,5,17β-triol, for the preparation of drospirenone, a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic activity, useful for preparing pharmaceutical compositions with contraceptive action.

Process for the preparation of drospirenone

A process is described, comprising the oxidation of 17α-(3-hydroxypropyl)-6β,7β,15β,16β-dimethylen-5β-androstan-3β,5,17β-triol, for the preparation of drospirenone, a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic activity, useful for preparing pharmaceutical compositions with contraceptive action.

Biocatalytic oxidation of 1,4-diols and γ-lactols into γ-lactones: Application to chemoenzymatic synthesis of drospirenone

Oxidation of 1-alkyl-1,4-butanediols with Acetobacter aceti MIM 2000/28 gave the corresponding γ-lactones in good yields. The biotransformation occurred with intermediate formation of γ-lactols, which are also substrates for oxidation with Acetobacter aceti MIM 2000/28, as validated by selective biotransformation of 6β,7β;15β,16β-dimethylene-3- oxo-17α-pregn-4-en-21,17-carbolactol to drospirenone.

PROCESS FOR THE PREPARATION OF DROSPIRENONE

It is described of a process for the preparation of drospirenone, the compound of formula 1 shown below, a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic activity, useful for preparing pharmaceutical compositions having contraceptive action, starting from 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triοΙ.