(+)-Norgestrel

Base Information

• Chemical Name: (+)-Norgestrel
• CAS No.: 797-64-8
• Deprecated CAS: 76497-12-6,150200-16-1,150200-16-1
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452
• European Community (EC) Number: 686-277-4
• UNII: Z2QG2679YT
• DSSTox Substance ID: DTXSID90892173
• Nikkaji Number: J76.208C
• Wikidata: Q27122247
• Metabolomics Workbench ID: 57563
• Mol file: 797-64-8.mol

Synonyms:dextronorgestrel;dextronorgestrel, (8alpha,17alpha)-(+-)-isomer

Chemical Property of (+)-Norgestrel

Chemical Property:

• Melting Point: 239-241?°C(lit.)
• Refractive Index: 1.4900 (estimate)
• Boiling Point: 392.36°C (rough estimate)
• PSA: 37.30000
• Density: 1.0697 (rough estimate)
• LogP: 3.88260
• 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:

95% ^*data from raw suppliers

L(+)-Norgestrel ^*data from reagent suppliers

Safty Information:

• 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@@]12CC[C@@H]3[C@@H]([C@H]1CC[C@@]2(C#C)O)CCC4=CC(=O)CC[C@@H]34
• Uses: L(+)-Norgestrel is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.

Technology Process of (+)-Norgestrel

There total 17 articles about (+)-Norgestrel 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:

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

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

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.