(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)

Base Information

• Chemical Name: (5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)
• CAS No.: 126690-41-3
• Molecular Formula: C32H45NO6
• Molecular Weight: 539.712
• Mol file: 126690-41-3.mol

Synonyms:(5A,11B)-11-[4-(DIMETHYLAMINO)PHENYL]-5,17-DIHYDROXY-19-NORPREGN-9-ENE-3,20-DIONE CYCLIC BIS(1,2-ETHANEDIYL ACETAL);(5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dionecyclicbis(1,2-ethanediylacetal);

Chemical Property of (5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)

Chemical Property:

• Boiling Point: 697.0±55.0 °C(Predicted)
• PKA: 14.69±0.70(Predicted)
• PSA: 80.62000
• Density: 1.27
• LogP: 4.51500

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)

There total 10 articles about (5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(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: 93.0%

3,3,20,20-bis(ethylenedioxy)-17α-hydroxy-5α,10α-epoxy-19-norpregna-9(11)-ene + 4-dimethylaminophenylmagnesium bromide (7353-91-5) → 3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene (126690-41-3)

Guidance literature:

With copper(l) iodide; dimethylsulfide; In tetrahydrofuran; at 20 ℃;

Reference yield: 76.0%

4-bromo-N,N-dimethylaniline (586-77-6) + 5α,10α-epoxy-17α-hydroxy-19-norpregn-9(11)-ene-3,20-dione 3,20-bis(ethylene acetal) (54201-83-1) → 3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene (126690-41-3)

Guidance literature:

4-bromo-N,N-dimethylaniline; With 1,1-Dibromoethane; iodine; magnesium; In tetrahydrofuran; for 1.5h;

5α,10α-epoxy-17α-hydroxy-19-norpregn-9(11)-ene-3,20-dione 3,20-bis(ethylene acetal); With copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0039-128X(00)00100-8

Reference yield: 46.0%

3,3,20,20-bis(ethylene-dioxy)-17α-hydroxy-5,10-epoxy-19-norpregn-9(11)-ene → 3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene (126690-41-3)

Guidance literature:

4-bromo-N,N-dimethylaniline; With magnesium; ethylene dibromide; In tetrahydrofuran; at 15 - 50 ℃; for 2.08333h;

3,3,20,20-bis(ethylene-dioxy)-17α-hydroxy-5,10-epoxy-19-norpregn-9(11)-ene; copper(l) chloride; In tetrahydrofuran; dichloromethane; at 15 - 25 ℃; for 2.75h;

With water; ammonium chloride; In tetrahydrofuran; dichloromethane; Product distribution / selectivity;

upstream raw materials:

4-bromo-N,N-dimethylaniline

5α,10α-epoxy-17α-hydroxy-19-norpregn-9(11)-ene-3,20-dione 3,20-bis(ethylene acetal)

17α-hydroxy-19-norpregna-5(10),9(11)-diene-3,20-dione 3,20-bis(ethylene acetal)

3,3-ethylenedioxy-17β-cyano-17α-chloromethyl(dimethyl)siloxy estren-5(10),9(11)diene

Downstream raw materials:

ulipristal acetate

CDB-3236

Refernces

• 1、 -. "Preparing acetic acid superior strengthsi Te key intermediate of the new method". . . Retrieved 2017/06/30.
• 2、 -. "ULIPRISTAL ACETATE PREPARATION METHOD AND INTERMEDIATE THEREOF". Paragraph 0043. . Retrieved 2014/09/29.