3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene

Base Information

• Chemical Name: 3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene
• CAS No.: 202062-90-6
• Molecular Formula: C₃₃H₄₇NO₆
• Molecular Weight: 553.739
• Mol file: 202062-90-6.mol

Synonyms:3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene

Chemical Property of 3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene

There total 8 articles about 3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene 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:

13β-ethyl-17β-hydroxy-18,19-dinor-17α-pregna-4,9-dien-20-yn-3-one (24881-79-6) → 3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene (202062-90-6)

Guidance literature:

Multi-step reaction with 6 steps

1: AcONO₂ / CH₂Cl₂ / 1 h / -15 °C

2: Hg(OAC)2 / dimethylformamide / 5.5 h / Ambient temperature

3: 89 percent / 0.5 M aq. KHCO₃ / methanol / a) RT, overnight, b) reflux, 1 h

4: 84 percent / TsOH*H₂O, triethylorthoformate / CH₂Cl₂ / Ambient temperature

5: 38 percent / 30percent aq. H₂O₂, (CF₃)2CO*3H₂O, Na₂HPO₄ / CH₂Cl₂ / a) 0 deg C, 3 h, b) 4 deg C, overnight

6: 1.) Mg, I₂, dibromomethane, 2.) CuCl / 1.) THF, reflux, 20 min, 2.) THF, RT, 1 h

With disodium hydrogenphosphate; nitro acetate; mercury(II) diacetate; dihydrogen peroxide; iodine; potassium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; orthoformic acid triethyl ester; Hexafluoroacetone; copper(l) chloride; 1,2-dibromomethane; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(97)00119-0

Reference yield:

13β-ethyl-17β-hydroxy-18,19-dinor-17α-pregn-5(10)-en-20-yn-3-one (19914-67-1) → 3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene (202062-90-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 66.8 percent / pyridinium bromide perbromide / pyridine / 1 h / 85 - 90 °C

2: AcONO₂ / CH₂Cl₂ / 1 h / -15 °C

3: Hg(OAC)2 / dimethylformamide / 5.5 h / Ambient temperature

4: 89 percent / 0.5 M aq. KHCO₃ / methanol / a) RT, overnight, b) reflux, 1 h

5: 84 percent / TsOH*H₂O, triethylorthoformate / CH₂Cl₂ / Ambient temperature

6: 38 percent / 30percent aq. H₂O₂, (CF₃)2CO*3H₂O, Na₂HPO₄ / CH₂Cl₂ / a) 0 deg C, 3 h, b) 4 deg C, overnight

7: 1.) Mg, I₂, dibromomethane, 2.) CuCl / 1.) THF, reflux, 20 min, 2.) THF, RT, 1 h

With disodium hydrogenphosphate; nitro acetate; mercury(II) diacetate; dihydrogen peroxide; iodine; pyridinium hydrobromide perbromide; potassium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; orthoformic acid triethyl ester; Hexafluoroacetone; copper(l) chloride; 1,1-dibromomethane; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(97)00119-0

Reference yield:

levonorgestrel (797-63-7) → 3,20-bis-ethylenedioxy-13β-ethyl-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-18,19-dinorpregn-9-ene (202062-90-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) ethylene glycol, p-TsOH*H₂O, 2.) glacial acetic acid, H₂O / 1.) benzene, reflux, 16 h, 2.) 50 deg C, 17 h

2: 66.8 percent / pyridinium bromide perbromide / pyridine / 1 h / 85 - 90 °C

3: AcONO₂ / CH₂Cl₂ / 1 h / -15 °C

4: Hg(OAC)2 / dimethylformamide / 5.5 h / Ambient temperature

5: 89 percent / 0.5 M aq. KHCO₃ / methanol / a) RT, overnight, b) reflux, 1 h

6: 84 percent / TsOH*H₂O, triethylorthoformate / CH₂Cl₂ / Ambient temperature

7: 38 percent / 30percent aq. H₂O₂, (CF₃)2CO*3H₂O, Na₂HPO₄ / CH₂Cl₂ / a) 0 deg C, 3 h, b) 4 deg C, overnight

8: 1.) Mg, I₂, dibromomethane, 2.) CuCl / 1.) THF, reflux, 20 min, 2.) THF, RT, 1 h

With disodium hydrogenphosphate; nitro acetate; mercury(II) diacetate; water; dihydrogen peroxide; iodine; pyridinium hydrobromide perbromide; potassium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; ethylene glycol; acetic acid; orthoformic acid triethyl ester; Hexafluoroacetone; copper(l) chloride; 1,1-dibromomethane; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(97)00119-0

upstream raw materials:

4-bromo-N,N-dimethylaniline

3,20-bis-ethylenedioxy-13β-ethyl-17α-hydroxy-5α,10α-epoxy-18,19-dinorpregn-9(11)-ene

13β-ethyl-17β-hydroxy-18,19-dinor-17α-pregn-5(10)-en-20-yn-3-one

13β-ethyl-17β-hydroxy-18,19-dinor-17α-pregna-4,9-dien-20-yn-3-one

Downstream raw materials:

(8S,11R,13S,14S,17R)-17-Acetyl-11-(4-dimethylamino-phenyl)-13-ethyl-17-hydroxy-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one