11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile

Base Information

• Chemical Name: 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile
• CAS No.: 91934-94-0
• Molecular Formula: C₃₂H₄₆N₂O₄Si
• Molecular Weight: 550.814
• Mol file: 91934-94-0.mol

Synonyms:11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile

Chemical Property of 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile

There total 2 articles about 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.71%

4-bromo-N,N-dimethylaniline (586-77-6) + 3,3-ethylendioxy-5α,10α-epoxy-17α-(trimethylsilyloxy)-estr-9(11)-en-17β-carbonitrile (33403-21-3) → 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile (91934-94-0)

Guidance literature:

4-bromo-N,N-dimethylaniline; With magnesium; ethylene dibromide; In tetrahydrofuran; toluene; at 14 - 60 ℃; Inert atmosphere; Industry scale;

3,3-ethylendioxy-5α,10α-epoxy-17α-(trimethylsilyloxy)-estr-9(11)-en-17β-carbonitrile; copper(l) chloride; In tetrahydrofuran; dichloromethane; toluene; at 8 - 25 ℃; Inert atmosphere; Industry scale;

With sodium metabisulfite; ammonium chloride; In tetrahydrofuran; dichloromethane; water; toluene; Product distribution / selectivity; Industry scale;

Reference yield: 80.0%

copper(I) chloride (7758-89-6) + 4-bromo-N,N-dimethylaniline (586-77-6) + 3,3-ethylendioxy-5α,10α-epoxy-17α-(trimethylsilyloxy)-estr-9(11)-en-17β-carbonitrile (33403-21-3) → 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile (91934-94-0)

Guidance literature:

With ammonium chloride; iodine; magnesium; In tetrahydrofuran;

Reference yield: 95.2%

11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile (91934-94-0) + chloromethyl methyl ether (107-30-2) → Telapristone (198414-30-1)

Guidance literature:

chloromethyl methyl ether; With biphenyl; lithium; In tetrahydrofuran; toluene; at -55 - -40 ℃; Inert atmosphere;

11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile; In tetrahydrofuran; toluene; at -55 - -50 ℃; for 3h;

With sulfuric acid; water; In tetrahydrofuran; toluene; at 20 ℃; for 2h; Reagent/catalyst; Temperature;

upstream raw materials:

copper(I) chloride

4-bromo-N,N-dimethylaniline

3,3-ethylendioxy-5α,10α-epoxy-17α-(trimethylsilyloxy)-estr-9(11)-en-17β-carbonitrile

Downstream raw materials:

11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5,17α-bis[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile

ulipristal acetate

CDB-3236

Telapristone acetate