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14340-01-3

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14340-01-3 Usage

Uses

Gestadienol is a progesterone (P755900) used in the study of human membrane progesterone receptor alpha (hu-mPRα) and nuclear progesterone receptor (nPR).

Check Digit Verification of cas no

The CAS Registry Mumber 14340-01-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,3,4 and 0 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 14340-01:
(7*1)+(6*4)+(5*3)+(4*4)+(3*0)+(2*0)+(1*1)=63
63 % 10 = 3
So 14340-01-3 is a valid CAS Registry Number.

14340-01-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 17-hydroxy-19-norpregna-4,9-diene-3,20-dione

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:14340-01-3 SDS

14340-01-3Synthetic route

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

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

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
With water; trifluoroacetic acid In tetrahydrofuran at 20℃; for 2h;77%
C25H35NO4

C25H35NO4

methyllithium
917-54-4

methyllithium

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: C25H35NO4; methyllithium In diethyl ether at 0 - 10℃; for 4h; Cooling with ice;
Stage #2: With hydrogenchloride; water In acetone at 25℃; for 8h; Solvent;
72%
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

methyllithium
917-54-4

methyllithium

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: 17α-[(±)1-(1-ethoxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene; methyllithium In diethyl ether at 0 - 10℃; for 4h;
Stage #2: With hydrogenchloride In acetone at 25℃; for 8h;
72%
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

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
With di-t-butyl biphenyl; lithium In tetrahydrofuran at -70℃; for 2.25h; Title compound not separated from byproducts;
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

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / DMAP; TEA / tetrahydrofuran / 20 °C
2: Li; di-t-butyl biphenyl / tetrahydrofuran / 2.25 h / -70 °C
View Scheme
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale
2.1: diethyl ether / 4 h / 0 - 10 °C / Cooling with ice
2.2: 8 h / 25 °C
View Scheme
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)

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

ethylene deltenone
5571-36-8

ethylene deltenone

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid / methanol / 20 °C / Large scale
2.1: ethyl vinyl ether; toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling with ice; Large scale
2.2: 8 h / 0 - 10 °C / Large scale
2.3: 4 h / 25 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / methanol / 20 °C / Large scale
2.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale
3.1: 2 h / 0 - 10 °C / Cooling with ice
3.2: 0.5 h
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / methanol / 20 °C / Large scale
2.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale
3.1: tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 - 10 °C / Cooling with ice
3.2: 2 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / methanol / 20 °C
2: toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling; Large scale
3: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Cooling; Large scale
View Scheme
ethylene deltenone
5571-36-8

ethylene deltenone

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid / methanol / 20 °C / Large scale
2.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale
3.1: diethyl ether / 4 h / 0 - 10 °C / Cooling with ice
3.2: 8 h / 25 °C
View Scheme
C25H35NO4

C25H35NO4

methyllithium
917-54-4

methyllithium

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: C25H35NO4; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice;
Stage #2: With hydrogenchloride; water In methanol at 25℃; for 2h; Solvent; Overall yield = 73%; Overall yield = 6.6 g;
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 8h; Cooling; Large scale; Overall yield = 1036 g;
C25H35NO4

C25H35NO4

methyl Grignard reagent

methyl Grignard reagent

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: C25H35NO4; methyl Grignard reagent at 0 - 10℃; for 2h; Cooling with ice;
Stage #2: With hydrogenchloride; water for 0.5h; Solvent; Overall yield = 68%; Overall yield = 2.1g;
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

methyllithium
917-54-4

methyllithium

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: 17α-[(±)1-(1-n-propyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; 2-methyltetrahydrofuran for 0.5h; Solvent; Overall yield = 70%; Overall yield = 4g;
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Overall yield = 70 %; Overall yield = 4.0 g;
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

methyllithium
917-54-4

methyllithium

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: 17α-[(±)1-(1-isobutyloxyl)ethyl]oxyl-17β-cyano-3,3-(ethylene-dioxy)-19-norpregna-5(10),9(11)-diene; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; 2-methyltetrahydrofuran for 0.5h; Solvent; Overall yield = 67%; Overall yield = 4.7g;
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Overall yield = 67 %; Overall yield = 4.7 g;
C26H35NO4

C26H35NO4

methyllithium
917-54-4

methyllithium

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: C26H35NO4; methyllithium In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; for 4h; Cooling with ice;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; 2-methyltetrahydrofuran for 0.5h; Solvent; Overall yield = 72%; Overall yield = 11.2 g;
methyllithium
917-54-4

methyllithium

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

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Stage #1: 3,3-(ethylene-dioxy)-17β-cyano-17α-hydroxy-19-norpregna-5(10),9(11)-diene With toluene-4-sulfonic acid; ethyl vinyl ether In tetrahydrofuran at 20℃; for 3h; Cooling with ice; Large scale;
Stage #2: methyllithium In tetrahydrofuran; diethyl ether at 0 - 10℃; for 8h; Large scale;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 25℃; for 4h; Large scale; Overall yield = 75%; Overall yield = 1036 g;
A n/a
B n/a
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

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale
2.1: 2 h / 0 - 10 °C / Cooling with ice
2.2: 0.5 h
View Scheme
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 20 °C / Cooling with ice; Large scale
2.1: tetrahydrofuran; 2-methyltetrahydrofuran / 4 h / 0 - 10 °C / Cooling with ice
2.2: 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 20 °C / Cooling; Large scale
2: tetrahydrofuran; diethyl ether / 8 h / 0 - 20 °C / Cooling; Large scale
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

methyllithium
917-54-4

methyllithium

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Overall yield = 72 %; Overall yield = 11.2 g;
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

methyllithium
917-54-4

methyllithium

A

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

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

B

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 10℃; Reagent/catalyst; Solvent; Overall yield = 73 %; Overall yield = 6.6 g;
3,3-dimethoxy-estra-5(10),9(11)-diene-17-one
10109-76-9

3,3-dimethoxy-estra-5(10),9(11)-diene-17-one

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium hydroxide / tetrahydrofuran; acetone / 2 h / 5 - 40 °C / Inert atmosphere
1.2: 1 h / 35 - 40 °C
2.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C
3.1: sodium methylate; methanol / 3 h / 60 - 65 °C
3.2: 1 h / Heating
4.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C
View Scheme
3,3-dimethoxy-21-(phenylsulfinyl)-19-norpregna-5(10),9(11),17(20),20-tetraene

3,3-dimethoxy-21-(phenylsulfinyl)-19-norpregna-5(10),9(11),17(20),20-tetraene

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium methylate; methanol / 3 h / 60 - 65 °C
1.2: 1 h / Heating
2.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C
View Scheme
3,3-(2,2-dimethyltrimethylene-1,3-dioxy)-5(10),9(11)-estradien-17-one
91175-92-7

3,3-(2,2-dimethyltrimethylene-1,3-dioxy)-5(10),9(11)-estradien-17-one

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium hydroxide / tetrahydrofuran; acetone / 2 h / 5 - 40 °C / Inert atmosphere
1.2: 1 h / 35 - 40 °C
2.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C
3.1: sodium methylate; methanol / 3 h / 60 - 65 °C
3.2: 1 h
4.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C
View Scheme
3,3-dimethoxy-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene

3,3-dimethoxy-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
With perchloric acid; acetic acid at 20 - 30℃; for 0.166667h;59 g
3,3-(2,2-dimethylpropylenedioxy)-17α-ethynyl-17β-hydroxyestra-5(10),9(11)-diene

3,3-(2,2-dimethylpropylenedioxy)-17α-ethynyl-17β-hydroxyestra-5(10),9(11)-diene

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C
2.1: sodium methylate; methanol / 3 h / 60 - 65 °C
2.2: 1 h
3.1: acetic acid; perchloric acid / 0.17 h / 20 - 30 °C
View Scheme
3,3-(propylenedioxy)estra-5(10),9(11)-diene-17-one

3,3-(propylenedioxy)estra-5(10),9(11)-diene-17-one

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium hydroxide / tetrahydrofuran; acetone / 2 h / 5 - 40 °C / Inert atmosphere
1.2: 1 h / 35 - 40 °C
2.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C
3.1: sodium methylate; methanol / 3 h / 60 - 65 °C
3.2: 1 h
4.1: hydrogenchloride / methanol; water / 0.17 h / 20 - 30 °C
View Scheme
3,3-(propylenedioxy)-21-(phenylsulfinyl)-19-norpregna-5(10),9(11),17(20),20-tetraene

3,3-(propylenedioxy)-21-(phenylsulfinyl)-19-norpregna-5(10),9(11),17(20),20-tetraene

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium methylate; methanol / 3 h / 60 - 65 °C
1.2: 1 h
2.1: hydrogenchloride / methanol; water / 0.17 h / 20 - 30 °C
View Scheme
3,3-(propylenedioxy)-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene.

3,3-(propylenedioxy)-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene.

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20 - 30℃; for 0.166667h;52 g
17α-hydroxy-20-methoxy-19-norpregna-4(5),9(10),20-trien-3-one

17α-hydroxy-20-methoxy-19-norpregna-4(5),9(10),20-trien-3-one

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20 - 30℃; for 1h;46 g
21-(phenylsulfinyl)-19-norpregna-4(5), 9(10),17(20),20-tetraene-3-one

21-(phenylsulfinyl)-19-norpregna-4(5), 9(10),17(20),20-tetraene-3-one

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium methylate; methanol / methanol / 2 h / 60 - 65 °C
1.2: 1 h / Heating
2.1: hydrogenchloride / methanol; water / 1 h / 20 - 30 °C
View Scheme
RU 3097
14531-92-1

RU 3097

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C
2.1: sodium methylate; methanol / methanol / 2 h / 60 - 65 °C
2.2: 1 h / Heating
3.1: hydrogenchloride / methanol; water / 1 h / 20 - 30 °C
View Scheme
3,3-(2,2-dimethylpropylenedioxy)-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene

3,3-(2,2-dimethylpropylenedioxy)-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
With perchloric acid; acetic acid at 20 - 30℃; for 0.166667h;51 g
3,3-(propylenedioxy)-17α-ethynyl-17β-hydroxyestra-5(10),9(11)-diene

3,3-(propylenedioxy)-17α-ethynyl-17β-hydroxyestra-5(10),9(11)-diene

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; acetic acid / methanol; water; dichloromethane / 0.5 h / -10 - 0 °C
2.1: sodium methylate; methanol / 3 h / 60 - 65 °C
2.2: 1 h
3.1: hydrogenchloride / methanol; water / 0.17 h / 20 - 30 °C
View Scheme
ethylene glycol
107-21-1

ethylene glycol

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

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)

Conditions
ConditionsYield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In dichloromethane at 20℃; Inert atmosphere;77%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In dichloromethane at 18 - 25℃; for 17h;4.2 g
acetic acid
64-19-7

acetic acid

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

17α-acetoxy-19-norpregna-4,9-diene-3,20-dione
14340-04-6

17α-acetoxy-19-norpregna-4,9-diene-3,20-dione

Conditions
ConditionsYield
With toluene-4-sulfonic acid; trifluoroacetic anhydride In dichloromethane at 0℃; for 0.25h;62.3%
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

3,20-bis-ethylenedioxy-5α,17α-dihydroxy-11β-[4-(2-methyl-1,3-dioxolan-2-yl)phenyl]-19-norpregn-9-ene

3,20-bis-ethylenedioxy-5α,17α-dihydroxy-11β-[4-(2-methyl-1,3-dioxolan-2-yl)phenyl]-19-norpregn-9-ene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / dichloromethane / 20 °C / Inert atmosphere
2.1: dihydrogen peroxide; Hexafluoroacetone; disodium hydrogenphosphate / dichloromethane / 0 - 5 °C
3.1: magnesium; iodine; ethylene dibromide / tetrahydrofuran / 2 h / Inert atmosphere; Heating
3.2: 1.25 h / 20 °C
View Scheme
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

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)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / dichloromethane / 20 °C / Inert atmosphere
2: dihydrogen peroxide; Hexafluoroacetone; disodium hydrogenphosphate / dichloromethane / 0 - 5 °C
View Scheme
17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione
14340-01-3

17α-hydroxy-19-norpregna-4(5),9(10)-diene-3,20-dione

trimethyl orthoformate
149-73-5

trimethyl orthoformate

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20 - 25℃; for 3h;62 g

14340-01-3Relevant articles and documents

Preparation method of ulipristal acetate diketal

-

Page/Page column 9-11, (2019/01/11)

The invention discloses a preparation method of ulipristal acetate diketal. Dihydroxyprogesterone dehydrogenate 1 is used as the raw material to prepare an important intermediate of sterides, namely ulipristal acetate diketal 8; a reaction formula is shown in the attached figure. The preparation method has the advantages that the dihydroxyprogesterone dehydrogenate 1 is used as a starting raw material, seven steps are performed, and the ulipristal acetate diketal with weight total yield rate of 65% or above can be obtained; the reaction is simple, the selectivity is good, and the preparation method is suitable for industrialization production.

Method for preparing ulipristal acetate and key intermediate thereof

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Paragraph 0103, (2014/10/16)

A method as well as new intermediates for preparing Ulipristal acetate (a compound I) and a method for preparing the new intermediates are provided. The intermediate in a constitutional formula IV is conductive to reacting with methyl lithium or methyl Grignard reagent, a protective group is easy to be removed after a reaction, side reactions are few, a mid-term treatment is simple, the reagents used are cheap, costs are low and a yield is high, if a compound in a constitutional formula V is obtained by the reaction of a compound in a constitutional formula III and the intermediate in the constitutional formula IV, the yield of a two-step reaction is 75%, a purity is above 98%. wherein R is defined in the specification.

METHOD FOR PREPARING 17 alpha-ACETOXY-11beta-(4-N,N-DIMETHYLAMINOPHENYL)-19-NORPREGNA-4,9-DIENE-3,20-DIONE, INTERMEDIATES THEREOF, AND METHODS FOR THE PREPARATION OF SUCH INTERMEDIATES

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Page 9-10, (2010/02/08)

Methods for the preparation of the 19-norprogesterone of formula I and its intermediates, in crystalline and amorphous forms.

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