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159811-51-5

159811-51-5

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  • High quality (8S,11R,13S,14S,17R)-17-acetyl-11-(4-(dimethylamino)phenyl)-1,2,7,8,11,12,13,15,16,17-decahydro-17-hydroxy-13-methyl-6H-cyclopenta[a]phenanthren-3(14H)-one supplier in China

    Cas No: 159811-51-5

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  • High Quality 99% 19-Norpregna-4,9-diene-3,20-dione,11-[4-(dimethylamino)phenyl]-17-hydroxy-, (11b)- 159811-51-5 ISO Manufacturer

    Cas No: 159811-51-5

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159811-51-5 Usage

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 159811-51-5 differently. You can refer to the following data:
1. Labelled Ulipristal. Ulipristal is a selective progesterone receptor modulator. Ulipristal is used during pregnancy.
2. Labelled Ulipristal (U700800). Ulipristal is a selective progesterone receptor modulator. Ulipristal is used during pregnancy.
3. Α selective progesterone receptor modulator

Check Digit Verification of cas no

The CAS Registry Mumber 159811-51-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,9,8,1 and 1 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 159811-51:
(8*1)+(7*5)+(6*9)+(5*8)+(4*1)+(3*1)+(2*5)+(1*1)=155
155 % 10 = 5
So 159811-51-5 is a valid CAS Registry Number.

159811-51-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (8S,11R,13S,14S,17R)-17-acetyl-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

1.2 Other means of identification

Product number -
Other names 6J5J15Q2X8

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:159811-51-5 SDS

159811-51-5Synthetic route

C31H43NO4

C31H43NO4

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃; for 1h; Industrial scale;98.2%
3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-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

CDB-3236
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;
11β-(4-N,N-dimethylaminophenyl)-17α-hydroxy-20-methoxy-19-norpregna-4,9,20-triene-3-one

11β-(4-N,N-dimethylaminophenyl)-17α-hydroxy-20-methoxy-19-norpregna-4,9,20-triene-3-one

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
With acetic acid In water at 25℃; for 1h;74%
With hydrogenchloride In methanol at 20℃; for 0.5h;70%
11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5,17α-bis[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile
1094602-02-4

11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5,17α-bis[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile

methyllithium
917-54-4

methyllithium

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Stage #1: 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5,17α-bis[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile; methyllithium With N,N,N,N,-tetramethylethylenediamine at -50 - -35℃; for 3h;
Stage #2: With water at 20℃;
Stage #3: With sulfuric acid In methanol at 40℃; for 3h;		70.7%
11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile
91934-94-0

11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile

methyllithium
917-54-4

methyllithium

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Stage #1: 11β-[4-(N,N-dimethylamino)phenyl]-3,3-ethylenedioxy-5α-hydroxy-17α-[(trimethylsilyl)oxy]-5α-estr-9-en-17β-carbonitrile; methyllithium With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -50 - -40℃; for 3h;
Stage #2: With water In tetrahydrofuran at 20℃;
Stage #3: With sulfuric acid In methanol at 40℃; for 3h;		70%
17α-hydroxy-19-norpregna-5(10),9(11)-diene-3,20-dione 3,20-bis(ethylene acetal)
54201-84-2

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 3 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
3.1: 88 percent / aq. H2SO4 / ethanol / 1 h / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
2.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
2.2: 2 h / 10 - 20 °C / Large scale
3.1: hydrogenchloride / 2 h / 25 °C
View Scheme
5α,10α-epoxy-17α-hydroxy-19-norpregn-9(11)-ene-3,20-dione 3,20-bis(ethylene acetal)
54201-83-1

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Mg; I2; dibromoethane / tetrahydrofuran / 1.5 h
1.2: 76 percent / CuCl / tetrahydrofuran / 1 h / 20 °C
2.1: 88 percent / aq. H2SO4 / ethanol / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
1.2: 2 h / 10 - 20 °C / Large scale
2.1: hydrogenchloride / 2 h / 25 °C
View Scheme
3,3-(ethylene-dioxy)-17β-cyano-17α-hydroxy-19-norpregna-5(10),9(11)-diene

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 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
5.1: 88 percent / aq. H2SO4 / ethanol / 1 h / Heating
View Scheme
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling; Large scale
2.1: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Cooling; Large scale
3.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
4.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
5.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
5.2: 2 h / 10 - 20 °C / Large scale
6.1: hydrogenchloride / 2 h / 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 4 h / 20 °C / Cooling; Large scale
2.1: tetrahydrofuran; 2-methyltetrahydrofuran / 0 - 10 °C
3.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
4.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
5.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
5.2: 2 h / 10 - 20 °C / Large scale
6.1: hydrogenchloride / 2 h / 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 4 h / 20 °C / Cooling; Large scale
2.1: tetrahydrofuran; 2-methyltetrahydrofuran / 0 - 10 °C
3.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
4.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
5.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
5.2: 2 h / 10 - 20 °C / Large scale
6.1: hydrogenchloride / 2 h / 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 4 h / 20 °C / Cooling; Large scale
2.1: tetrahydrofuran; 2-methyltetrahydrofuran / 0 - 10 °C
3.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
4.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
5.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
5.2: 2 h / 10 - 20 °C / Large scale
6.1: hydrogenchloride / 2 h / 25 °C
View Scheme
3,3-ethylenedioxy-17β-cyano-17α-chloromethyl(dimethyl)siloxy estren-5(10),9(11)diene
290825-36-4

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 4 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
4.1: 88 percent / aq. H2SO4 / ethanol / 1 h / Heating
View Scheme
3-(ethylenedioxy)estra-5α,10α-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene
137532-55-9

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: triethylamine; acetic acid / Inert atmosphere
3.1: sodium methylate / methanol
4.1: Acidic conditions
View Scheme
Multi-step reaction with 5 steps
1.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: sulfuric acid / water; ethanol / 2 h / 70 °C / Inert atmosphere
3.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
4.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
4.2: 2 h / 70 °C / Inert atmosphere
5.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 45 °C / Industrial scale
1.2: 0 °C / Industrial scale
2.1: triethylamine / dichloromethane / 0.08 h / 0 °C / Industrial scale
2.2: 2 h / -5 - 0 °C / Industrial scale
3.1: methanol / 2.5 h / 70 °C / Industrial scale
3.2: 5 h / 70 °C / Industrial scale
4.1: hydrogenchloride / methanol; water / 1 h / 20 °C / Industrial scale
View Scheme
4-bromo-N,N-dimethylaniline
586-77-6

4-bromo-N,N-dimethylaniline

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: triethylamine; acetic acid / Inert atmosphere
3.1: sodium methylate / methanol
4.1: Acidic conditions
View Scheme
Multi-step reaction with 5 steps
1.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: sulfuric acid / water; ethanol / 2 h / 70 °C / Inert atmosphere
3.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
4.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
4.2: 2 h / 70 °C / Inert atmosphere
5.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium / tetrahydrofuran; dichloromethane / 3 h / 40 - 50 °C / Large scale
1.2: 2 h / 10 - 20 °C / Cooling with ice; Large scale
2.1: hydrogenchloride; water / 2 h / 25 °C
View Scheme
3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne
91934-95-1

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; acetic acid / Inert atmosphere
2: sodium methylate / methanol
3: Acidic conditions
View Scheme
Multi-step reaction with 4 steps
1.1: sulfuric acid / water; ethanol / 2 h / 70 °C / Inert atmosphere
2.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
3.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
3.2: 2 h / 70 °C / Inert atmosphere
4.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water / 25 °C
1.2: 25 °C
2.1: triethylamine / dichloromethane / -60 °C
3.1: methanol / 6 h / 64 - 65 °C
4.1: acetic acid / water / 1 h / 25 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water / 25 °C
1.2: 25 °C
2.1: triethylamine / dichloromethane / 0.5 h / 25 - 30 °C
3.1: methanol / 6 h / 64 - 65 °C
4.1: acetic acid / water / 1 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 0.08 h / 0 °C / Industrial scale
1.2: 2 h / -5 - 0 °C / Industrial scale
2.1: methanol / 2.5 h / 70 °C / Industrial scale
2.2: 5 h / 70 °C / Industrial scale
3.1: hydrogenchloride / methanol; water / 1 h / 20 °C / Industrial scale
View Scheme
3-(ethylenedioxy)estra-5,10-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: triethylamine; acetic acid / Inert atmosphere
3.1: sodium methylate / methanol
4.1: Acidic conditions
View Scheme
Multi-step reaction with 5 steps
1.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: sulfuric acid / water; ethanol / 2 h / 70 °C / Inert atmosphere
3.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
4.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
4.2: 2 h / 70 °C / Inert atmosphere
5.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
17α-ethynyl-17β-hydroxy-11β-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3-one

17α-ethynyl-17β-hydroxy-11β-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3-one

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
2.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
2.2: 2 h / 70 °C / Inert atmosphere
3.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / -60 °C
2: methanol / 6 h / 64 - 65 °C
3: acetic acid / water / 1 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0.5 h / 25 - 30 °C
2: methanol / 6 h / 64 - 65 °C
3: acetic acid / water / 1 h / 25 °C
View Scheme
11β-(4-N,N-dimethylaminophenyl)-21-(phenyl-sulfinyl)-19-norpregna-4,9,17(20),20-tetraene-3-one

11β-(4-N,N-dimethylaminophenyl)-21-(phenyl-sulfinyl)-19-norpregna-4,9,17(20),20-tetraene-3-one

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
1.2: 2 h / 70 °C / Inert atmosphere
2.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: methanol / 6 h / 64 - 65 °C
2: acetic acid / water / 1 h / 25 °C
View Scheme
3-(ethylenedioxy)estra-5,10-epoxy-9(11)-ene-17-one
786698-67-7

3-(ethylenedioxy)estra-5,10-epoxy-9(11)-ene-17-one

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
2.2: 1 h / 0 °C / Inert atmosphere
3.1: triethylamine; acetic acid / Inert atmosphere
4.1: sodium methylate / methanol
5.1: Acidic conditions
View Scheme
Multi-step reaction with 6 steps
1.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
2.2: 1 h / 0 °C / Inert atmosphere
3.1: sulfuric acid / water; ethanol / 2 h / 70 °C / Inert atmosphere
4.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
5.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
5.2: 2 h / 70 °C / Inert atmosphere
6.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol
5490-76-6

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Hexafluoroacetone; dihydrogen peroxide; sodium phosphate dibasic dodecahydrate / water; dichloromethane / Inert atmosphere
2.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
2.2: 1 h / 0 °C / Inert atmosphere
3.1: triethylamine; acetic acid / Inert atmosphere
4.1: sodium methylate / methanol
5.1: Acidic conditions
View Scheme
Multi-step reaction with 6 steps
1.1: Hexafluoroacetone; dihydrogen peroxide; sodium phosphate dibasic dodecahydrate / water; dichloromethane / Inert atmosphere
2.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
2.2: 1 h / 0 °C / Inert atmosphere
3.1: sulfuric acid / water; ethanol / 2 h / 70 °C / Inert atmosphere
4.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
5.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
5.2: 2 h / 70 °C / Inert atmosphere
6.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: disodium hydrogenphosphate; dihydrogen peroxide / dichloromethane / 18 h / 20 °C / Industrial scale
2.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 45 °C / Industrial scale
2.2: 0 °C / Industrial scale
3.1: triethylamine / dichloromethane / 0.08 h / 0 °C / Industrial scale
3.2: 2 h / -5 - 0 °C / Industrial scale
4.1: methanol / 2.5 h / 70 °C / Industrial scale
4.2: 5 h / 70 °C / Industrial scale
5.1: hydrogenchloride / methanol; water / 1 h / 20 °C / Industrial scale
View Scheme
C36H43NO4S

C36H43NO4S

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium methylate / methanol
2: Acidic conditions
View Scheme
C31H43NO5

C31H43NO5

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Acidic conditions;
ethylene deltenone
5571-36-8

ethylene deltenone

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetrahydrofuran / 0 °C
2.1: Hexafluoroacetone; dihydrogen peroxide; sodium phosphate dibasic dodecahydrate / water; dichloromethane / Inert atmosphere
3.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
3.2: 1 h / 0 °C / Inert atmosphere
4.1: triethylamine; acetic acid / Inert atmosphere
5.1: sodium methylate / methanol
6.1: Acidic conditions
View Scheme
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / 0 °C
2.1: Hexafluoroacetone; dihydrogen peroxide; sodium phosphate dibasic dodecahydrate / water; dichloromethane / Inert atmosphere
3.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
3.2: 1 h / 0 °C / Inert atmosphere
4.1: sulfuric acid / water; ethanol / 2 h / 70 °C / Inert atmosphere
5.1: triethylamine / tetrahydrofuran / 2 h / -78 - -70 °C / Inert atmosphere
6.1: sodium methylate / methanol / 1 h / 70 °C / Inert atmosphere
6.2: 2 h / 70 °C / Inert atmosphere
7.1: hydrogenchloride / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: acetic acid / methanol / 20 °C
2.1: toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling; Large scale
3.1: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Cooling; Large scale
4.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
5.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
6.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
6.2: 2 h / 10 - 20 °C / Large scale
7.1: hydrogenchloride / 2 h / 25 °C
View Scheme
3,3,20,20-bis(ethylene-dioxy)-17α-hydroxy-5β,10β-epoxy-19-norpregna-9(11)-ene

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: magnesium / tetrahydrofuran; dichloromethane / 3 h / 40 - 50 °C / Large scale
1.2: 2 h / 10 - 20 °C / Cooling with ice; Large scale
2.1: hydrogenchloride; water / 2 h / 25 °C
View Scheme
17α-[(±)1-(1-n-propyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

17α-[(±)1-(1-n-propyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran; 2-methyltetrahydrofuran / 0 - 10 °C
2.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
3.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
4.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
4.2: 2 h / 10 - 20 °C / Large scale
5.1: hydrogenchloride / 2 h / 25 °C
View Scheme
17α-[(±)1-(1-isobutyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

17α-[(±)1-(1-isobutyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran; 2-methyltetrahydrofuran / 0 - 10 °C
2.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
3.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
4.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
4.2: 2 h / 10 - 20 °C / Large scale
5.1: hydrogenchloride / 2 h / 25 °C
View Scheme
17α-[(±)1-(1-tetrahydropyran)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

17α-[(±)1-(1-tetrahydropyran)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran; 2-methyltetrahydrofuran / 0 - 10 °C
2.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
3.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
4.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
4.2: 2 h / 10 - 20 °C / Large scale
5.1: hydrogenchloride / 2 h / 25 °C
View Scheme
17α-hydroxy-19-norpregna-5(10),9(11)-diene-3,20-dione

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
2.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
3.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
3.2: 2 h / 10 - 20 °C / Large scale
4.1: hydrogenchloride / 2 h / 25 °C
View Scheme
3,3,20,20-bis(ethylenedioxy)-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl]-19-norgestrel-9(11)-ene

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

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
With hydrogenchloride at 25℃; for 2h;
C25H35NO4

C25H35NO4

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Cooling; Large scale
2.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
3.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
4.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
4.2: 2 h / 10 - 20 °C / Large scale
5.1: hydrogenchloride / 2 h / 25 °C
View Scheme
17α-[(±)1-(1-ethoxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

17α-[(±)1-(1-ethoxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrahydrofuran; 2-methyltetrahydrofuran / 0 - 10 °C
2.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 5 h / 20 - 25 °C / Large scale
3.1: Hexafluoroacetone; dihydrogen peroxide / dichloromethane; pyridine / -5 - 5 °C / Large scale
4.1: magnesium; copper(l) chloride / tetrahydrofuran / 3 h / 25 - 50 °C / Large scale
4.2: 2 h / 10 - 20 °C / Large scale
5.1: hydrogenchloride / 2 h / 25 °C
View Scheme
11β-(4-N,N-dimethylaminophenyl)-21-(phenyl-sulfinyl)-19-norpregna-4,9,17(20),20-tetraene-3-one

11β-(4-N,N-dimethylaminophenyl)-21-(phenyl-sulfinyl)-19-norpregna-4,9,17(20),20-tetraene-3-one

A

11β-(4-(N,N-dimethylamino)phenyl)-17β-hydroxy-19-norpregna-4,9-diene-3,20-dione

11β-(4-(N,N-dimethylamino)phenyl)-17β-hydroxy-19-norpregna-4,9-diene-3,20-dione

B

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Stage #1: 11β-(4-N,N-dimethylaminophenyl)-21-(phenyl-sulfinyl)-19-norpregna-4,9,17(20),20-tetraene-3-one With sodium methylate; phosphorous acid trimethyl ester
Stage #2: With hydrogenchloride
C24H34O6

C24H34O6

CDB-3236
159811-51-5

CDB-3236

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium; copper dichloride / tetrahydrofuran; ethylene dibromide / 2.5 h / 10 - 25 °C
2: hydrogenchloride / water / 2 h / 25 °C
View Scheme
acetic anhydride
108-24-7

acetic anhydride

CDB-3236
159811-51-5

CDB-3236

ulipristal acetate
126784-99-4

ulipristal acetate

Conditions
ConditionsYield
Stage #1: acetic anhydride With perchloric acid at -10℃; Inert atmosphere;
Stage #2: CDB-3236 In dichloromethane at -30 - -20℃; for 2h; Inert atmosphere;		93.4%
Stage #1: acetic anhydride; CDB-3236 With perchloric acid In dichloromethane at -10℃; for 3h; Industrial scale;
Stage #2: With pyrographite In isopropyl alcohol for 0.5h; Industrial scale;		90.9%
With perchloric acid In dichloromethane at -25 - -20℃; for 0.833333h;85%
trifluoroacetic anhydride
96-63-9

trifluoroacetic anhydride

CDB-3236
159811-51-5

CDB-3236

ulipristal acetate
126784-99-4

ulipristal acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 0.333333h;68%
CDB-3236
159811-51-5

CDB-3236

11β-(4-N-methylaminophenyl)-17α-hydroxy-19-norpregna-4,9-diene-3,20-dione
159681-67-1

11β-(4-N-methylaminophenyl)-17α-hydroxy-19-norpregna-4,9-diene-3,20-dione

Conditions
ConditionsYield
With iodine; calcium oxide In tetrahydrofuran; methanol

159811-51-5Relevant articles and documents

Acetic acid wu lisi he and its intermediate preparation method

-

Paragraph 0022; 0102-0104, (2017/09/19)

The invention discloses a preparation method of ulipristal acetate and an intermediate thereof, and belongs to the field of pharmaceutical synthesis. The preparation method of the ulipristal acetate comprises the following steps: by taking 3,3-(ethylenedioxy)-19-methylestra-5(10),9(11)-diene-3,17-diketone as raw material, enabling the raw material to react with sodium acetylide or potassium acetylide to obtain a compound III, carrying out high-selectivity epoxidation by oxide to obtain a compound IV, subsequently enabling the compound IV to react with 4-(N,N-dimethyl amino) phenyl magnesium bromide Grignard reagent to obtain a compound V, then enabling the compound V to react with phenyl sulfonic acid chloride to obtain a compound VI, enabling the compound VI to respectively react with sodium methoxide and trimethyl phosphate to obtain a compound VII, hydrolyzing and removing a protection group to obtain a compound VIII, finally carrying out acetylation reaction to obtain the ulipristal acetate, wherein the reaction formulae are as shown in the description. The method is short in synthetic route, mild in reaction conditions, high in yield and purity of products, low in cost, stable and controllable in quality, and is suitable for industrial production.

Ulipristal acetate impurities and preparation and detection method thereof

-

, (2016/10/31)

The invention provides ulipristal acetate impurity compounds and a preparation method thereof, and particularly provides novel compound impurities including A (a compound A), G (a compound G), H (a compound H) and J (a compound J). The invention further provides a detection method of the impurities and application of the impurities on quality analysis of an ulipristal acetate bulk drug and a preparation thereof.

First synthesis and characterization for the stereoisomers of Ulipristal acetate

Zhao, Yi,Li, Xiaolong,Liu, Hong,Yu, Yongguo,Hai, Li,Guo, Li,Wu, Yong

, p. 7 - 16 (2015/01/30)

The three stereoisomers, 11α,17α-isomer I, 11α,17β-isomer II and 11β,17β-isomer III are related substances of the selective progesterone receptor modulator Ulipristal acetate. Herein, we presented an efficient and practical synthesis approach to deliver t

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