(5α,11β,17α)-11-[4-(diMethylaMino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-one Cyclic 1,2-Ethanediyl Acetal

Base Information

• Chemical Name: (5α,11β,17α)-11-[4-(diMethylaMino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-one Cyclic 1,2-Ethanediyl Acetal
• CAS No.: 91934-95-1
• Molecular Formula: C₃₀H₃₉NO₄
• Molecular Weight: 477.644
• Mol file: 91934-95-1.mol

Synonyms:3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne

Chemical Property of (5α,11β,17α)-11-[4-(diMethylaMino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-one Cyclic 1,2-Ethanediyl Acetal

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

(5α,11β,17α)-11-[4-(dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-oneCyclic1,2-EthanediylAcetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the synthesis of 17β-side chain mifepristone analogues that act as progesterone receptor anatagonists.

Technology Process of (5α,11β,17α)-11-[4-(diMethylaMino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-one Cyclic 1,2-Ethanediyl Acetal

There total 8 articles about (5α,11β,17α)-11-[4-(diMethylaMino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-one Cyclic 1,2-Ethanediyl Acetal 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: 61.2%

4-bromo-N,N-dimethylaniline (586-77-6) + 3-(ethylenedioxy)estra-5α,10α-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene (137532-55-9) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne (91934-95-1)

Guidance literature:

4-bromo-N,N-dimethylaniline; With magnesium; In tetrahydrofuran; ethylene dibromide; at 45 ℃; for 3h; Industrial scale;

3-(ethylenedioxy)estra-5α,10α-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene; With copper(l) chloride; In tetrahydrofuran; ethylene dibromide; at 0 ℃; Industrial scale;

Reference yield: 50.4%

4-bromo-N,N-dimethylaniline (586-77-6) + 3-(ethylenedioxy)estra-5,10-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne (91934-95-1)

Guidance literature:

4-bromo-N,N-dimethylaniline; With iodine; magnesium; In tetrahydrofuran; at 20 - 50 ℃; Inert atmosphere;

3-(ethylenedioxy)estra-5,10-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene; With copper(l) chloride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.steroids.2013.09.009

Reference yield:

ethylene deltenone (5571-36-8) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne (91934-95-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 36 percent / NaHCO₃; mCPBA / CH₂Cl₂ / 0.5 h / -40 °C

2: 45 percent / CuCl / tetrahydrofuran / 1 h / 20 °C

3: 90 percent / tetrahydrofuran / 16 h / 20 °C

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.steroids.2006.07.003

upstream raw materials:

4-bromo-N,N-dimethylaniline

3-(ethylenedioxy)estra-5α,10α-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one

ethylene deltenone

Downstream raw materials:

C₃₇H₄₅NO₆S

3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester

CDB-3236

ulipristal acetate