(10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

Base Information

• Chemical Name: (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS No.: 6533-00-2
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452
• Hs Code.: 2937230000
• European Community (EC) Number: 229-433-5
• NSC Number: 759653
• Wikipedia: Norgestrel
• Wikidata: Q27163551
• NCI Thesaurus Code: C703
• RXCUI: 7518
• ChEMBL ID: CHEMBL4571597
• Mol file: 6533-00-2.mol

Synonyms:18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-(+-)-;DL Norgestrel;DL-Norgestrel;Neogest;Norgestrel;Ovrette;Postinor;Wy 3707;Wy-3707;Wy3707

Chemical Property of (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 239-241 °C(lit.)
• Refractive Index: 1.571
• Boiling Point: 459.139 °C at 760 mmHg
• PKA: 13.09±0.40(Predicted)
• Flash Point: 195.446 °C
• PSA: 37.30000
• Density: 1.139 g/cm³
• LogP: 3.88260
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Sonicated), Dichloromethane (Slightly), Methanol (Slightly
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 312.208930132
• Heavy Atom Count: 23
• Complexity: 609

Purity/Quality:

99.00% ^*data from raw suppliers

Norgestrel ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
• Isomeric SMILES: CC[C@]12CCC3[C@H]4CCC(=O)C=C4CCC3C1CC[C@]2(C#C)O
• Recent ClinicalTrials: Adherence With Continuous-dose Oral Contraceptive: Evaluation of Self-Selection and Use
• Description: Norgestrel is a synthetic progestin and a racemic mixture of dextronorgestrel and levonorgestrel , of which levonorgestrel is the biologically active component. In vivo, norgestrel administered via intrauterine device (IUD) prevents pregnancy in rats. Formulations containing nogestrel have been used as contraceptives.
• Uses: Progestogen; oral contraceptive. The bioactive enantiomer is levorotatory A metabolite of Norgestrel. A glucuronide metabolite of Levonorgestrel. An intermediate to the glucuronide metabolite of Levonorgestrel. It is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive. analgesic, antipyretic

Technology Process of (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

There total 17 articles about (10R,13S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

13β-ethyl-3-methoxy-17α-ethynyl-gona-2,5(10)-dien-17β-ol (799-43-9,14507-51-8,19640-66-5,24377-29-5) → levonorgestrel (797-63-7,797-64-8,6533-00-2,17092-09-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at -10 ℃; Temperature; Solvent;

Reference yield:

2-Ethyl-3-vinyl-cyclopentanone → norgestrel (797-63-7,797-64-8,17092-09-0,6533-00-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent NaH, Et₃N / 1,2-dimethoxy-ethane; paraffin / 1.) 3.5 h, reflux; 2.) 40 min

2: 1.) 2,4,6-trimethylphenol, pyridine; 2.) oxalic acid / 1.) methylcyclohexane, 13.5 h, 98 deg C, irradiation

3: 99 percent / LiAlH₄ / diethyl ether

4: 62 percent / K, aniline, NH₃ / tetrahydrofuran / 1 h

5: 76 percent / 2-butanone, aluminium isopropylate, mol. sieve / benzene

6: 0.16 g / LDA / tetrahydrofuran

With pyridine; lithium aluminium tetrahydride; molecular sieve; Mesitol; ammonia; oxalic acid; aluminum isopropoxide; sodium hydride; triethylamine; aniline; butanone; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; paraffin; benzene;

DOI:10.1002/hlca.19850680430

Reference yield:

(5R,8R,9S,10R,13S,14S)-13-Ethyl-5-hydroxy-3-methyl-tetradecahydro-4-oxa-cyclopenta[a]phenanthren-17-one (23855-42-7,35442-18-3,35442-19-4) → norgestrel (797-63-7,797-64-8,17092-09-0,6533-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NBS / acetone

2: (i) liq. NH₃ (ii) /BRN= 4147360/, benzene, Et₂O

With N-Bromosuccinimide; In acetone;

DOI:10.1002/hlca.19710540852

upstream raw materials:

13β-ethyl-3-methoxy-17α-ethynyl-gona-2,5(10)-dien-17β-ol

(+/-)-13β-Ethylgon-4-ene-3,17-dione

acetylene

dl-3-methoxy-13β-ethylgona-2,5(10)-dien-17-one

Downstream raw materials:

DL-17β-Hydroxy-13β.17α-diethyl-gon-4-en-3-on

13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one

13β-ethyl-18,19-dinor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol

Refernces

• 1、 Baier,Durner,Quinkert. "Total-synthesis of (-)-norgestrel". . p. 1054 - 1068. Retrieved 2007/10/02.
• 2、 Rosenberger,Fraher,Saucy. "Steroid total synthesis. IV.(+)-13 -ethyl-17 -ethynyl-17 -hydroxy-gon-4-en-3-one.". . p. 2857 - 2870. Retrieved 2007/10/06.