Desogestrel supplier | CasNO.54024-22-5

Name
Desogestrel
EINECS 258-929-4
CAS No. 54024-22-5
Article Data20
CAS DataBase
Density 1.07 g/cm³
Solubility practically insoluble in water
Melting Point 109-110 ºC
Formula C₂₂H₃₀O
Boiling Point 428.3 ºC at 760 mmHg
Molecular Weight 310.48
Flash Point 187.9 ºC
Transport Information
Appearance white to off-white crystalline powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Desogen;18,19-Dinorpregn-4-en-20-yn-17-ol,13-ethyl-11-methylene-, (17a)-;3-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol;
PSA 20.23000
LogP 4.86970

Synthetic route

: C24H38O2Si

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water Solvent; Reflux;	96.5%

: 1216963-74-4
lithium acetylide-ethylenediamine complex

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 21h;	89%

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

: 1066-54-2
trimethylsilylacetylene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-hexyllithium In tetrahydrofuran; hexane at -5℃; for 0.5h; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran; hexane at 0 - 5℃; for 1h;	89%

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

: 74-86-2
acetylene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
With lithium; ethylenediamine In tetrahydrofuran at 25℃; for 2h; continuous flow of ethyne;	85%
Stage #1: acetylene With lithium In ethylenediamine at 20℃; for 2h; Peterson olefination; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran at 20℃; for 2h; Further stages;	83%
Stage #1: acetylene With N,N,N,N,-tetramethylethylenediamine; lithium for 2h; Stage #2: 11-methylene-18a-homo-estr-4-en-17-one In tetrahydrofuran at 20℃; for 2h; Stage #3: With hydrogenchloride; water In tetrahydrofuran	83%

: 116930-33-7
C24H32OS2

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
With sodium In tetrahydrofuran; ammonia at -4℃; for 1h;	58%

: 1216963-74-4
lithium acetylide-ethylenediamine complex

: 54024-21-4
11-methylene-18a-homo-estr-4-en-17-one

A: 54024-22-5
desogestrel

B: 16β-OH desogestrel

Conditions

Conditions	Yield
In tetrahydrofuran; ethylenediamine at 10 - 20℃; for 4h;	A 0.220 g B 0.060 g

...Expand

: 220332-76-3
(+)-(1S,3aS,7aS)-hexahydro-1-(tert-butyldimethylsiloxy)-7a-ethyl-5-indanone

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 80 percent / NaH, MeOH / tetrahydrofuran; hexane / 1 h / Heating 2: 1.) NaH, 2.) n-BuLi 3: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 4: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 6: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 7: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 8: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 9: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 10: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 11: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 12: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 12 steps
1: 80 percent / NaH, MeOH / tetrahydrofuran; hexane / 1 h / Heating
2: 1.) NaH, 2.) n-BuLi
3: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h
4: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C
5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C
6: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
7: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
8: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
9: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
10: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
11: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
12: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: 220332-77-4
(+)-(1S,3aS,7aS)-3a,4,7,7a-tetrahydro-1-(tert-butyldimethylsiloxy)-6-carbomethoxy-7a-ethyl-5-hydroxyindane

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) NaH, 2.) n-BuLi 2: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 3: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 4: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 5: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 6: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 7: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 8: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 9: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 10: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 11: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) NaH, 2.) n-BuLi
2: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h
3: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C
4: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C
5: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
6: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
7: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
8: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
9: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
10: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
11: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: 54024-20-3
(+)-13β-ethyl-11-methylenegona-4-en-17β-ol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 2: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

: 220332-82-1
(+)-13β-ethyl-17β-hydroxy-11-methylenegona-4-en-3-one

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 2: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 3: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 4: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

: 220332-79-6
11-carbomethoxy-13-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraen-17β-ol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 2: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 3: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 4: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 5: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 6: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 7: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 8: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 9: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 9 steps
1: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C
2: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C
3: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
4: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
5: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
6: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
7: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
8: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
9: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: 54024-19-0
(+)-13β-ethyl-3,3-ethylenedithio-11-methylenegona-4-en-17β-ol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 2: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 3: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

: 161640-05-7
17β-(tert-butyldimethylsiloxy)-13-ethyl-11-methylene-3-methoxygona-1,3,5(10)-triene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 2: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 3: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 4: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 5: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 6: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

: 220332-81-0
17β-(tert-butyldimethylsiloxy)-13-ethyl-11-(hydroxymethyl)-3-methoxygona-1,3,5(10),9(11)-tetraene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 2: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 3: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 4: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 5: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 6: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 7: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 7 steps
1: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
2: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
3: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
4: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
5: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
6: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
7: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: 220332-78-5
(+)-(1S,3aS,4S,7aS)-3a,4,7,7a-tetrahydro-1-(tert-butyldimethylsiloxy)-6-carbomethoxy-7a-ethyl-5-hydroxy-4-(2-(3-methoxyphenyl)ethyl)indane

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h 2: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C 3: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 4: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 5: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 6: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 7: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 8: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 9: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 10: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 10 steps
1: 1.) trifluoroacetic acid, 2.) K2CO3, MeOH / 1.) CH2Cl2, 23 deg C, 24 h, 2.) 23 deg C, 1 h
2: 73 percent / imidazole / dimethylformamide / 12 h / 50 °C
3: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C
4: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
5: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
6: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
7: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
8: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
9: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
10: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: 220332-80-9
17β-(tert-butyldimethylsiloxy)-11-carbomethoxy-13-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C 2: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C 3: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C 4: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 5: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 6: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 7: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 8: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

Yield

Multi-step reaction with 8 steps
1: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 23 °C
2: 85 percent / DEAD, PPh3, o-NO2PhSO2NHNH2 / tetrahydrofuran / 14 h / -40 - 23 °C
3: liq. NH3, Li / ethanol; tetrahydrofuran / 1 h / -78 °C
4: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C
5: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C
6: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating
7: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C
8: 1.) n-BuLi, 2.) Ce(III) chloride
View Scheme

: tert-butyl-(13-ethyl-3-methoxy-11-methylene-2,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yloxy)-dimethyl-silane

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1 M aq. HCl, 48 percent aq. HF / tetrahydrofuran / 20 h / 23 °C 2: 100 percent / BF3*Et2O / methanol / 2 h / 23 °C 3: Li, liq. NH3 / tetrahydrofuran / 0.5 h / Heating 4: 99 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 23 °C 5: 1.) n-BuLi, 2.) Ce(III) chloride View Scheme

: 54024-17-8
13β-ethyl-11-methylenegon-4-en-3,17-dione

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 2: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 4: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 5: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme
Multi-step reaction with 3 steps 1: 91 percent / BF3*Et2O / tetrahydrofuran / 2.75 h / Heating 2: t-BuOK / tetrahydrofuran / 2 h / -20 - -15 °C 3: 58 percent / Na / liquid ammonia; tetrahydrofuran / 1 h / -4 °C View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride / 1,2-dimethoxyethane; 1,4-dioxane / -10 °C 1.2: 3 h / -15 - -10 °C 1.3: 0.67 h 2.1: sodium tetrahydroborate; water / ethanol / 0 - 20 °C 3.1: zinc; acetic acid / water / 12 h / 20 °C 4.1: sodium carbonate / water; tetrahydrofuran; dichloromethane / 0.17 h / 20 °C 4.2: 20 °C 5.1: ethylenediamine; lithium / tetrahydrofuran / 5 h / 30 - 50 °C View Scheme

: 54024-18-9
13-ethyl-11-methylenegon-4-ene-3,17-dione cyclic 3-(1,2-ethanediyl dithioacetal)

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 2: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 3: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 4: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme
Multi-step reaction with 2 steps 1: t-BuOK / tetrahydrofuran / 2 h / -20 - -15 °C 2: 58 percent / Na / liquid ammonia; tetrahydrofuran / 1 h / -4 °C View Scheme

: 53067-82-6
13β-ethyl-11α-hydroxygon-5-ene-3,17-dione

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 94 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 2: 79 percent / HC(OEt)3, p-TsOHH2O / CH2Cl2 / 7 h / Heating 3: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C 4: 74 percent / p-TsOHH2O / formic acid / 7 h / 50 - 60 °C 5: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 6: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 7: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 8: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 9: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

Yield

Multi-step reaction with 9 steps
1: 94 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C
2: 79 percent / HC(OEt)3, p-TsOH*H2O / CH2Cl2 / 7 h / Heating
3: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C
4: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C
5: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C
6: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature
7: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C
8: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C
9: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h
View Scheme

: 196716-43-5
13β-ethyl-gona-5-ene-3,11,17-trione-3,17-diethylene ketal

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C 2: 74 percent / p-TsOHH2O / formic acid / 7 h / 50 - 60 °C 3: 98 percent / BF3Et2O / methanol / 2.5 h / 0 - 5 °C 4: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 5: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 6: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 7: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

Yield

Multi-step reaction with 7 steps
1: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C
2: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C
3: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C
4: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature
5: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C
6: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C
7: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h
View Scheme

: 100071-90-7
18-methyl-estra-4-en-3,11,17-trione

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 79 percent / HC(OEt)3, p-TsOHH2O / CH2Cl2 / 7 h / Heating 2: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C 3: 74 percent / p-TsOHH2O / formic acid / 7 h / 50 - 60 °C 4: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 5: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 6: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 7: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 8: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

Yield

Multi-step reaction with 8 steps
1: 79 percent / HC(OEt)3, p-TsOH*H2O / CH2Cl2 / 7 h / Heating
2: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C
3: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C
4: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C
5: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature
6: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C
7: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C
8: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h
View Scheme

: 196716-46-8
D-13β-Ethyl-11-methylenegon-4-en-17α-ol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 2: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

: 196716-45-7
D-13β-Ethyl-3,3-ethylenedithio-11-methylenegon-4-ene-17α-ol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 2: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 3: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

: 196716-44-6
D-13β-Ethyl-11β-hydroxy-11α-methylgon-5-ene-3,11-dione-3,17-diethylene ketal

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 74 percent / p-TsOHH2O / formic acid / 7 h / 50 - 60 °C 2: 98 percent / BF3Et2O / methanol / 2.5 h / 0 - 5 °C 3: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 4: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 5: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 6: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme

Yield

Multi-step reaction with 6 steps
1: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C
2: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C
3: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature
4: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C
5: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C
6: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h
View Scheme

: 160683-92-1
13-ethyl-gona-4-ene-11α,17β-diol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 2: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 3: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 4: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 5: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme

Yield

Multi-step reaction with 5 steps
1: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature
2: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C
3: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification
4: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature
5: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne
View Scheme

: 160683-93-2
18a-homo-estr-4-ene-11,17-dione

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 2: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 3: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 4: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran; hexane / 15 - 30 °C 2: tetrahydrofuran; hexane / Reflux 3: hydrogenchloride / methanol; water / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 1.5 h / 0 - 10 °C 1.2: 1.5 h / 25 °C 2.1: n-hexyllithium / tetrahydrofuran; hexane / 0.5 h / -5 °C 2.2: 1 h / 0 - 5 °C View Scheme

: 160683-85-2
3-methoxy-18a-homo-estra-2,5(10)-diene-11α,17β-diol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 92 percent / HCl / acetone; H2O 2: boron trifluoride diethyl ether / methanol / 1 h / Ambient temperature 3: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 4: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 5: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 6: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 7: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 8: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme

Yield

Multi-step reaction with 8 steps
1: 92 percent / HCl / acetone; H2O
2: boron trifluoride diethyl ether / methanol / 1 h / Ambient temperature
3: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C
4: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature
5: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C
6: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification
7: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature
8: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne
View Scheme

: 160683-91-0
3,3-ethylenedithio-18a-homo-estr-4-ene-11α,17β-diol

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C 2: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature 3: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C 4: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification 5: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 6: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme

Yield

Multi-step reaction with 6 steps
1: 87 percent / Li, ethylamine / tetrahydrofuran / 0.5 h / -35 - -30 °C
2: 85 percent / SO3 pyridine complex / triethylamine; dimethylsulfoxide / 3 h / Ambient temperature
3: 85 percent / triethylorthoformate, p-toluenesulfonic acid hydrate / 3 h / 40 °C
4: 85 percent / NaH / dimethylsulfoxide; toluene / 12 h / 80 °C / sonification
5: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature
6: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne
View Scheme

: 160683-95-4
11-methylene-17-<(2,2-dimethyl)propane-1,3-dioxy>-18a-homo-estr-4-ene

: 54024-22-5
desogestrel

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid hydrate / acetone / 12 h / Ambient temperature 2: 85 percent / Li, ethylenediamine / tetrahydrofuran / 2 h / 25 °C / continuous flow of ethyne View Scheme

: 201230-82-2
carbon monoxide

: 2-(2-(1-phenylethylidene)hydrazinyl)pyridine

: 54024-22-5
desogestrel

: 2-{(8S,9S,10R,13S,14S,17S)-13-ethyl-17-hydroxy-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With dimanganese decacarbonyl In toluene at 100℃; under 760.051 Torr; for 16h; Schlenk technique; Sealed tube;	86%

...Expand

: 766-77-8
Dimethylphenylsilane

: 54024-22-5
desogestrel

: (8S,9S,10R,13S,14S,17S)-17-((dimethyl(phenyl)silyl)ethynyl)-13-ethyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions

Conditions	Yield
With potassium hydroxide In 1,2-dimethoxyethane at 45℃; for 48h;	60%

: 54024-22-5
desogestrel

: 106-95-6
allyl bromide

: 17-O-allyldesogestrel

Conditions

Conditions	Yield
Stage #1: desogestrel With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;	58%

: 54024-22-5
desogestrel

: 91781-33-8
17α-Bromethinyl-18-methyl-11-methylen-4-oestren-17β-ol

Conditions

Conditions	Yield
With N-Bromosuccinimide; silver nitrate In acetone for 0.75h; Ambient temperature;	51%

: 108-24-7
acetic anhydride

: 54024-22-5
desogestrel

: 160683-96-5
Acetic acid (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions

Conditions	Yield
With perchloric acid In toluene for 1h; Ambient temperature;

Desogestrel Chemical Properties

IUPAC Name: (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
Molecular Formula: C₂₂H₃₀O
Molecular Weight: 310.48 g/mol
SMILES: C1C(=C)[C@H]2[C@H]([C@@H]3CC[C@@](C#C)(O)[C@@]13CC)CCC=1[C@@H]2CCCC1
InChI: InChI=1/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
EINECS: 258-929-4
Classification Code: Contraceptive Agents; Contraceptive Agents, Female; Contraceptives, Oral; Contraceptives, oral, synthetic; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Progestin; Progestins; Reproductive Control Agents; Reproductive Effect
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals; Steroids
Index of Refraction: 1.566
Molar Refractivity: 94.23 cm³
Molar Volume: 288.7 cm³
Polarizability: 37.35×10^-24 cm³
Surface Tension: 43.9 dyne/cm
Density: 1.07 g/cm³
Flash Point: 187.9 °C
Enthalpy of Vaporization: 78.92 kJ/mol
Boiling Point: 428.3 °C at 760 mmHg
Melting Point: 109-110 °C
Vapour Pressure of Desogestrel (CAS NO.54024-22-5): 3.92E-09 mmHg at 25 °C

Desogestrel Uses

Desogestrel (CAS NO.54024-22-5) is a molecule used in hormonal contraceptives and as a progestogen with low androgenic potency.

Desogestrel Safety Profile

Human reproductive effects by ingestion: changes in menstrual cycle and female fertility. Experimental reproductive effects. A steroid. When heated to decomposition it emits acrid smoke and fumes.

Desogestrel Specification

Desogestrel (CAS NO.54024-22-5), its Synonyms are Desogen ; 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol ; Cerazette ; Desogestrelum ; 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17alpha)- .

Product Name

Desogestrel

Synthetic route

Desogestrel Chemical Properties

Desogestrel Uses

Desogestrel Safety Profile

Desogestrel Specification

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