11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol

Base Information

• Chemical Name: 11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol
• CAS No.: 1372163-83-1
• Molecular Formula: C₂₇H₃₅NO₃
• Molecular Weight: 421.58
• Mol file: 1372163-83-1.mol

Synonyms:11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol

Chemical Property of 11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol

There total 12 articles about 11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol 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: 85.0%

RU 39411 → 11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol (1372163-83-1)

Guidance literature:

RU 39411; With carbonochloridic acid 1-chloro-ethyl ester; In dichloromethane; at 0 ℃; for 24.5h; Reflux;

With methanol; for 3h; Reflux;

DOI:10.1021/bc200645n

Reference yield:

(11R,13S)-11-(4-(2-(dimethylamino)ethoxy)phenyl)-13-methyl-7,8,11,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione → 11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol (1372163-83-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic anhydride / dichloromethane / 16 h / 20 °C

2.1: sodium tetrahydroborate / methanol / 1 h / 20 °C

3.1: sodium hydroxide / methanol / 16 h / 20 °C

4.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 24.5 h / 0 °C / Reflux

4.2: 3 h / Reflux

With sodium tetrahydroborate; carbonochloridic acid 1-chloro-ethyl ester; acetic anhydride; sodium hydroxide; In methanol; dichloromethane;

DOI:10.1021/bc200645n

Reference yield:

ethylene deltenone (5571-36-8) → 11β-[4-(2-methylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-3,17β-diol (1372163-83-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine; dihydrogen peroxide; Hexafluoroacetone / dichloromethane / 18 h / 0 - 20 °C

2.1: copper(l) iodide / tetrahydrofuran / 0.25 h / -10 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: water; acetic acid / 1.5 h / 50 - 60 °C

4.1: caesium carbonate / acetone / 16 h / 80 °C

5.1: acetic anhydride / dichloromethane / 16 h / 20 °C

6.1: sodium tetrahydroborate / methanol / 1 h / 20 °C

7.1: sodium hydroxide / methanol / 16 h / 20 °C

8.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 24.5 h / 0 °C / Reflux

8.2: 3 h / Reflux

With pyridine; sodium tetrahydroborate; copper(l) iodide; carbonochloridic acid 1-chloro-ethyl ester; water; dihydrogen peroxide; acetic anhydride; caesium carbonate; acetic acid; Hexafluoroacetone; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/bc200645n

upstream raw materials:

3-acetoxy-11β-[4-(2-dimethylamino-ethoxy)-phenyl]-estra-1,3,5(10)-triene-17-one

(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

11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione

Downstream raw materials:

11β-(4-{2-[(2-{2-[2-(2-azido-ethoxy)-ethoxy]-ethoxy}-ethyl)-methyl-amino]-ethoxy}-phenyl)-estra-1,3,5(10)-triene-3,17β-diol