190662-30-7

Basic information

• Product Name: (17α)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile
• Synonyms: (17α)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile;(17alpha)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile;2-[(8S,13S,14S,17R)-17-hydroxy-13-methylspiro[1,2,4,6,7,8,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-yl]acetonitrile
• CAS NO: 190662-30-7
• Molecular Formula: C22H29NO3
• Molecular Weight: 355.47056
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 190662-30-7.mol

Chemical Properties

• Boiling Point: 565.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• PKA: 13.62±0.40(Predicted)
• CAS DataBase Reference: (17α)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (17α)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile(190662-30-7)
• EPA Substance Registry System: (17α)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile(190662-30-7)

Safety Data

• Hazardous Substances Data: 190662-30-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(17α)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile is used as an intermediate compound for the production of Dienogest (D441870), which is a derivative of 19-Nortestosterone (N315000). Dienogest is an oral contraceptive that is typically used in combination with estrogen to provide effective birth control.
Application Reason:
The compound's role as an intermediate in the synthesis of Dienogest is significant due to the contraceptive's widespread use and effectiveness in preventing pregnancy when taken in combination with estrogen. Dienogest's mechanism of action involves the inhibition of ovulation, alteration of cervical mucus to impede sperm penetration, and modification of the endometrium to prevent implantation of a fertilized egg.

Upstream product

• 5571-36-8 ethylene deltenone 
• 75-05-8 acetonitrile 

Downstream Products

• 65928-58-7 Dienogest 
• 106111-42-6 17α-Cyanomethyl-17β-hydroxy-estra-5(10),9(11)-dien-3-on 

Relevant articles and documents

Preparation method of dienogest

The invention relates to a preparation method of dienogest. The preparation method comprises the following steps: providing a compound with a structure shown as a formula (II); and carrying out an acidolysis deprotection reaction on the compound shown in the formula (II) in an aqueous fluoboric acid solution to prepare a compound with a structure shown in a formula (I). According to the preparation method of the dienogest, the problems of low purity and dark color of a crude product of an acidolysis deprotection process are fundamentally solved, a production process is greatly simplified, andthe production cost of an enterprise is reduced.

Preparation method of dienogest and method for recovering dienogest from dienogest mother liquor

The invention belongs to the technical field of steroid hormone drug preparation, and particularly relates to a preparation method of dienogest and a method for recovering the dienogest from dienogestmother liquor. The preparation method of the dienogest comprises the following steps: dissolving 17 alpha-cyanomethyl-17 beta-hydroxyl-5, 9-androstane diene-3, 17-diketone-3,3-ethyleneketal, adding fluoboric acid, carrying out acidolysis to remove protection, and after the reaction is completed, carrying out treatment to obtain the dinogestrol. The method for recovering the dienogestrol from thedienogestrol mother liquor comprises the following steps: dissolving the dienogestrol with a solvent to obtain the dienogestrol mother liquor, adding perchloric acid or concentrated hydrochloric acid,reacting for a period of time, heating to 45-55 DEG C, concentrating under reduced pressure, removing part of the solvent by concentrating until a solid is separated out, stopping concentrating, cooling, continuing the reaction, and treating to obtain the dienogestrol. The product provided by the invention has high purity and high yield.

Method for the preparation of steroid derivative ketal

The invention relates to a method for the preparation of a compound of formula II: STR1 wherein a compound of formula V: STR2 is condensed with a compound of the formula CH3 -C(OR4 O)-(CH2)3 -XHal and R1, R2, R3, R4, X and Hal are as defined by the specification.