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126690-41-3
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Basic Information
CAS No.: 126690-41-3
Name: (5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal)
Molecular Structure:
Molecular Structure of 126690-41-3 ((5a,11b)-11-[4-(Dimethylamino)phenyl]-5,17-dihydroxy-19-norpregn-9-ene-3,20-dione cyclic bis(1,2-ethanediyl acetal))
Formula: C32H45NO6
Molecular Weight: 539.712
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);
EINECS: 1592732-453-0
Density: 1.27
Boiling Point: 697.0±55.0 °C(Predicted)
PSA: 80.62000
LogP: 4.51500
Related products
Synthetic route

3,3,20,20-bis(ethylenedioxy)-17α-hydroxy-5α,10α-epoxy-19-norpregna-9(11)-ene

7353-91-5

4-dimethylaminophenylmagnesium bromide

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
With copper(l) iodide; dimethylsulfide In tetrahydrofuran at 20℃;93%
586-77-6

4-bromo-N,N-dimethylaniline

54201-83-1

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

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
Stage #1: 4-bromo-N,N-dimethylaniline With 1,1-Dibromoethane; iodine; magnesium In tetrahydrofuran for 1.5h;
Stage #2: 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; Grignard reaction;		76%

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

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
Stage #1: 4-bromo-N,N-dimethylaniline With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 50℃; for 2.08333h;
Stage #2: 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;
Stage #3: With water; ammonium chloride In tetrahydrofuran; dichloromethane Product distribution / selectivity;		46%
54201-84-2

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

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 54.3 percent / 30 percent H2O2; (CF3)2CO*3H2O; Na2HPO4 / CH2Cl2 / 7.5 h / 4 °C
2.1: Mg; I2; dibromoethane / tetrahydrofuran / 1.5 h
2.2: 76 percent / CuCl / tetrahydrofuran / 1 h / 20 °C
View Scheme

3,3-(ethylene-dioxy)-17β-cyano-17α-hydroxy-19-norpregna-5(10),9(11)-diene

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 98 percent / DMAP; TEA / tetrahydrofuran / 20 °C
2.1: Li; di-t-butyl biphenyl / tetrahydrofuran / 2.25 h / -70 °C
2.2: HC(OEt)3; p-TsOH / CH2Cl2 / 20 °C
3.1: 54.3 percent / 30 percent H2O2; (CF3)2CO*3H2O; Na2HPO4 / CH2Cl2 / 7.5 h / 4 °C
4.1: Mg; I2; dibromoethane / tetrahydrofuran / 1.5 h
4.2: 76 percent / CuCl / tetrahydrofuran / 1 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: dmap; triethylamine / tetrahydrofuran / 12 h / 5 - 20 °C
2.1: copper(I) bromide / tetrahydrofuran; toluene / 23 h / 20 °C
3.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C
3.2: 0.42 h / 4 °C
4.1: copper(l) iodide; dimethylsulfide / tetrahydrofuran / 20 °C
View Scheme
290825-36-4

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

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Li; di-t-butyl biphenyl / tetrahydrofuran / 2.25 h / -70 °C
1.2: HC(OEt)3; p-TsOH / CH2Cl2 / 20 °C
2.1: 54.3 percent / 30 percent H2O2; (CF3)2CO*3H2O; Na2HPO4 / CH2Cl2 / 7.5 h / 4 °C
3.1: Mg; I2; dibromoethane / tetrahydrofuran / 1.5 h
3.2: 76 percent / CuCl / tetrahydrofuran / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: copper(I) bromide / tetrahydrofuran; toluene / 23 h / 20 °C
2.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / dichloromethane / 18 h / 20 °C
2.2: 0.42 h / 4 °C
3.1: copper(l) iodide; dimethylsulfide / tetrahydrofuran / 20 °C
View Scheme
586-77-6

4-bromo-N,N-dimethylaniline

3,3,20,20-bis(ethylene-dioxy)-17α-hydroxy-5β,10β-epoxy-19-norpregna-9(11)-ene

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
Stage #1: 4-bromo-N,N-dimethylaniline With magnesium In tetrahydrofuran; dichloromethane at 40 - 50℃; for 3h; Large scale;
Stage #2: 3,3,20,20-bis(ethylene-dioxy)-17α-hydroxy-5β,10β-epoxy-19-norpregna-9(11)-ene With copper(l) chloride In tetrahydrofuran; dichloromethane at 10 - 20℃; for 2h; Cooling with ice; Large scale;		957g
586-77-6

4-bromo-N,N-dimethylaniline

C24H34O6

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
With magnesium; copper dichloride In tetrahydrofuran; ethylene dibromide at 10 - 25℃; for 2.5h;

C24H34O5

126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dihydrogen peroxide; pyridine; 1,1,1,3,3,3-hexafluoro-2-propanone trihydrate / dichloromethane / -10 - 5 °C
2: magnesium; copper dichloride / tetrahydrofuran; ethylene dibromide / 2.5 h / 10 - 25 °C
View Scheme
126690-41-3

3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene

159811-51-5

CDB-3236

Conditions
ConditionsYield
With sulfuric acid In ethanol for 1h; Heating;88%
Stage #1: 3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene With potassium hydrogensulfate; water at 5℃; for 4h;
Stage #2: With potassium hydroxide; water In dichloromethane Product distribution / selectivity;
With hydrogenchloride; water at 25℃; for 2h;
With hydrogenchloride In water at 25℃; for 2h;
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