60282-87-3

Basic information

• Product Name: Gestodene
• Synonyms: (8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one;17-alpha-Ethynyl-13-ethyl-17-beta-hydroxy-4,15-gonadien-3-one;18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha);(17R)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one;15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,12-dien-5-one;Gestodene Methyl analogue: 17alpha-(1-Propyn-1-yl)-17a-hydroxy-18-Methyl-4,15-estradien-3-one;(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one;(8R,9S,10R,13S,14S,17S)-13-ethyl-17-ethynyl-17-hydroxy-1,7,8,10,11,12,13,17-octahydro-2H-cyclopenta[a]phenanthren-3(6H,9H,14H)-one
• CAS NO: 60282-87-3
• Molecular Formula: C₂₁H₂₆O₂
• Molecular Weight: 310.43
• EINECS: 262-145-8
• Product Categories: Steroid and Hormone;Hormone Drugs;Miscellaneous Biochemicals;Hormone;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 60282-87-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 190-192°C
• Boiling Point: 462.7 °C at 760 mmHg
• Flash Point: 196.9 °C
• Appearance: white to off-white/
• Density: 1.15 g/cm³
• Vapor Pressure: 1.66E-10mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: >20mg/mL
• PKA: 12.16±0.40(Predicted)
• Merck: 14,4413
• CAS DataBase Reference: Gestodene(CAS DataBase Reference)
• NIST Chemistry Reference: Gestodene(60282-87-3)
• EPA Substance Registry System: Gestodene(60282-87-3)

Safety Data

• Hazard Codes: Xn
• Statements: 62
• Safety Statements: 36/37-24/25
• WGK Germany: 3
• RTECS: JF7956000
• Hazardous Substances Data: 60282-87-3(Hazardous Substances Data)

Usage

Description

Gestodene is a progestogen, recently launched in combination with ethinyl estradiol as an oral contraceptive.Gestodene is a steroid. It has a role as an estrogen.Gestodene, one of three new gonane progestins, is the most potent on a per weight basis in regard to progestational effects and has little or no estrogenic effect. In in vivo animal studies, gestodene also has less androgenic activity compared with progestins found in older combination oral contraceptive formulations.

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 60282-87-3 differently. You can refer to the following data:
1. Gestodene is an orally active gestogen with a progesterone-like profile of activity. Gestodene is used in combination with estrogen as an oral contraceptive.
2. Orally active gestogen with progesterone-like profile of activity. Used in combination with estrogen as oral contraceptive.
3. Estrogens and progestins are female hormones. They are produced by the body and are necessary for the normal sexual development of the female and for the regulation of the menstrual cycle during the childbearing years. Gestodene is a progestogen hormonal

Brand name

Femodene

InChI:InChI=1/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

Synthetic route

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-5,15-estradiene → gestodene (60282-87-3)

Conditions	Yield
With hydrogenchloride In acetone at 20℃; for 0.75h;	90%

17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol (64133-14-8) + 3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene → gestodene (60282-87-3)

Conditions	Yield
Stage #1: 17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol; 3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene With water; hydrogenchloride In acetone at 20℃; for 0.75h; Stage #2: With sodium hydrogencarbonate In water; acetone pH=7; Product distribution / selectivity;	90%

3-ethoxy-18-methyl-estra-3,5,15-trien-17-one (1323980-05-7) + acetylenemagnesium bromide (4301-14-8) → gestodene (60282-87-3)

Conditions	Yield
Stage #1: 3-ethoxy-18-methyl-estra-3,5,15-trien-17-one; acetylenemagnesium bromide In tetrahydrofuran; 2-MeTHF at 20 - 25℃; for 2h; Stage #2: With hydrogenchloride In ethanol; water at 7 - 10℃; for 2h;	80%

17α-Ethinyl-3,3-ethylendithio-18-methyl-4,15-estradien-17β-ol (74177-02-9) → gestodene (60282-87-3)

Conditions	Yield
With calcium carbonate; methyl iodide In methanol; water for 20h; Heating;	68%

ethylene glycol (107-21-1) + 15α-Acetoxy-18-methyl-4-estren-3,17-dion (104933-97-3) + acetylene (74-86-2) → gestodene (60282-87-3)

Conditions	Yield
Yield given. Multistep reaction;

18-Methyl-4,15-estradien-3,17-dion (77410-09-4) + acetylene (74-86-2) → gestodene (60282-87-3)

Conditions	Yield
With n-butyllithium 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h; Yield given. Multistep reaction;

15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on (104934-00-1) + acetylene (74-86-2) → gestodene (60282-87-3)

Conditions	Yield
Yield given. Multistep reaction;

13β-ethyl-gon-4-en-3,17-dione (21800-83-9) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 90 percent / triethyl orthoformate; p-TsOH / CH2Cl2 / 3 h / 10 °C 2.1: t-BuOK / tetrahydrofuran / 0.17 h / 20 °C 2.2: tetrahydrofuran / 2 h / 20 °C 3.1: Et3N / xylene / 2.5 h / 140 °C 4.1: 94 percent / tetrahydrofuran / 2 h / 0 °C 5.1: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: 90 percent / triethyl orthoformate; p-TsOH / CH2Cl2 / 3 h / 10 °C 2: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 - 20 °C 3: MCPBA / CH2Cl2 / 0.5 h / -78 °C 4: Et3N / xylene / 2.5 h / 140 °C 5: 94 percent / tetrahydrofuran / 2 h / 0 °C 6: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 77.2 percent / mushroom Penicillium raistrickii (ATCC 10490) / H2O; various solvent(s) / 70 h / 30 °C 2: 96 percent / pyridine / 1 h View Scheme

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-18-methyl-5,15-estradien-17-one → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran / 2 h / 0 °C 2: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme

18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5-estern-17-one → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: t-BuOK / tetrahydrofuran / 0.17 h / 20 °C 1.2: tetrahydrofuran / 2 h / 20 °C 2.1: Et3N / xylene / 2.5 h / 140 °C 3.1: 94 percent / tetrahydrofuran / 2 h / 0 °C 4.1: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 - 20 °C 2: MCPBA / CH2Cl2 / 0.5 h / -78 °C 3: Et3N / xylene / 2.5 h / 140 °C 4: 94 percent / tetrahydrofuran / 2 h / 0 °C 5: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme

C30H40O3S → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: MCPBA / CH2Cl2 / 0.5 h / -78 °C 2: Et3N / xylene / 2.5 h / 140 °C 3: 94 percent / tetrahydrofuran / 2 h / 0 °C 4: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-18-methyl-16ξ-phenylsulfoxide-5-estren-17-one → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / xylene / 2.5 h / 140 °C 2: 94 percent / tetrahydrofuran / 2 h / 0 °C 3: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme

15α-Hydroxy-18-methyl-4-estren-3,17-dion (60919-46-2) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / pyridine / 1 h View Scheme
Multi-step reaction with 3 steps 1: 96 percent / pyridine / 1 h 2: 84 percent / 4-CH3-C6H6-SO3H*C5H5N / 6 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 98 percent / BF3*Et2O / methanol / Ambient temperature 2: pyridine / 3.5 h / 0 °C 3: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 4: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 5: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme
Multi-step reaction with 3 steps 1: pyridine / 3.5 h / 0 °C 2: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 3: 1.) 15 percent BuLi / 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h View Scheme

3,3-Ethylendithio-18-methyl-4,15-estradien-17-on (74177-01-8) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 2: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme

3,3-Ethylendithio-15α-hydroxy-18-methyl-4-estren-17-on (74177-00-7) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 3.5 h / 0 °C 2: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 3: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 4: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme

15α-Acetoxy-18-methyl-4-estren-3,17-dion (104933-97-3) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / 4-CH3-C6H6-SO3H*C5H5N / 6 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / ethanol / 1 h / 20 °C 2.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / 1 h / 20 °C 2.2: 2 h / 40 °C 3.1: tetrahydrofuran; 2-MeTHF / 2 h / 20 - 25 °C 3.2: 2 h / 7 - 10 °C View Scheme

Methanesulfonic acid (8R,9S,10R,13S,14S,15S)-13-ethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl ester (104934-02-3) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 2: 1.) 15 percent BuLi / 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h View Scheme

C22H32O4S3 (104934-03-4) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 2: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 3: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme

15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on (104934-00-1) → gestodene (60282-87-3)

Conditions	Yield
Product distribution / selectivity;

ethyl bromide (74-96-4) + acetylene (74-86-2) → gestodene (60282-87-3)

Conditions	Yield
With oxalic acid; magnesium In tetrahydrofuran; methanol; water

15α-acetoxy-3-ethoxy-18-methyl-estra-3,5-dien-17-one (106620-51-3) → gestodene (60282-87-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / 1 h / 20 °C 1.2: 2 h / 40 °C 2.1: tetrahydrofuran; 2-MeTHF / 2 h / 20 - 25 °C 2.2: 2 h / 7 - 10 °C View Scheme

15α-Acetoxy-18-methyl-4-estren-3,17-dion (104933-97-3) + acetylene (74-86-2) → gestodene (60282-87-3)

Conditions	Yield
Stage #1: 15α-Acetoxy-18-methyl-4-estren-3,17-dion With hydrogenchloride; propylene glycol In 1,4-dioxane; 1,2-dimethoxyethane at -20℃; for 4h; Stage #2: With toluene-4-sulfonic acid; trimethyl orthoformate In methanol at 20℃; for 3h; Stage #3: acetylene Further stages;	8.17 g

gestodene (60282-87-3) → 17α-Bromethinyl-17β-hydroxy-18-methyl-4,15-oestradien-3-on (91781-31-6)

Conditions	Yield
With N-Bromosuccinimide; silver nitrate In acetone for 0.25h; Ambient temperature;	82%

gestodene (60282-87-3) → 17β-Hydroxy-17α-iodethinyl-18-methyl-4,15-oestradien-3-on (91798-46-8)

Conditions	Yield
With N-iodo-succinimide; silver nitrate In acetone for 0.25h; Ambient temperature;	77%

gestodene (60282-87-3) → 13-β-ethyl-18,19-dinorpregna-4,14,16-trien-3,20-dione

Conditions	Yield
With hydrogenchloride at 80℃; for 2h;	1.55 g

gestodene (60282-87-3) → gestodene propionate

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; propionic acid anhydride

pentanoic anhydride (2082-59-9) + gestodene (60282-87-3) → gestodene valerate

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine In pyridine; water

gestodene (60282-87-3) + 1-hexadecylcarboxylic acid (57-10-3) + trifluoroacetic anhydride (407-25-0) → 17α-ethynyl-17β-hexadecanoyloxy-18-methyl-4,15-estradien-3-one

Conditions	Yield
With sodium hydroxide In dichloromethane; acetone; benzene

undecylenic acid (112-37-8) + gestodene (60282-87-3) + trifluoroacetic anhydride (407-25-0) → 17α-ethynyl-18-methyl-17β-undecanoyloxy-4,15-estradien-3-one

Conditions	Yield
In benzene

gestodene (60282-87-3) + trifluoroacetic anhydride (407-25-0) → 17α-ethynyl-18-methyl-17β-octanoyloxy-4,15-estradien-3-one

Conditions	Yield
In dichloromethane; acetone; benzene

gestodene (60282-87-3) → 17β-acetoxy-17α-ethynyl-18-methyl-4,15-estradien-3-one

Conditions	Yield
With acetic anhydride In 2,3,5-trimethyl-pyridine; hydrogenchloride

Upstream product

• 104933-97-3 15α-Acetoxy-18-methyl-4-estren-3,17-dion 
• 74-86-2 acetylene 
• 106620-51-3 15α-acetoxy-3-ethoxy-18-methyl-estra-3,5-dien-17-one 
• 1323980-05-7 3-ethoxy-18-methyl-estra-3,5,15-trien-17-one 
• 4301-14-8 acetylenemagnesium bromide 
• 74-96-4 ethyl bromide 
• 104934-00-1 15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on 
• 64133-14-8 17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol 
• 104934-03-4 C₂₂H₃₂O₄S₃ 
• 104934-02-3 Methanesulfonic acid (8R,9S,10R,13S,14S,15S)-13-ethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl ester 
• 74177-00-7 3,3-Ethylendithio-15α-hydroxy-18-methyl-4-estren-17-on 
• 74177-01-8 3,3-Ethylendithio-18-methyl-4,15-estradien-17-on 
• 60919-46-2 15α-Hydroxy-18-methyl-4-estren-3,17-dion 
• 21800-83-9 13β-ethyl-gon-4-en-3,17-dione 

Downstream Products

• 932388-88-0 13-β-ethyl-18,19-dinorpregna-4,14,16-trien-3,20-dione 

Relevant articles and documents

A simple synthesis of gestodene from 18-methyl-4-estren-3,17-dione

A simple synthesis enables us to obtain the progestin, gestodene, in five steps and satisfactory yields from 18-methyl-4-estren-3,17-dione. This was accomplished through the selective protection of the C-3 carbonyl group as a cyclic ketal and the installation of a phenylsulfoxide group at the C-16 position.

Process for the preparation of gestodene

The invention relates to a process for the preparation of a compound of formula (I) : wherein R1 and R2 are as defined in the description, by reaction of a compound of formula (II) with a base. Compound (I) is an intermediate useful in the preparation of gestodene.

KIT FOR FEMALE MAMMALS, COMPRISING A COMBINATION OF GESTAGEN AND OESTROGEN

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