4,14-Dihydroxy-3-methoxy-N-methyl-6-oxomorphinan

Base Information

• Chemical Name: 4,14-Dihydroxy-3-methoxy-N-methyl-6-oxomorphinan
• CAS No.: 6199-38-8
• Molecular Formula: C18H23NO4
• Molecular Weight: 318.38746
• DSSTox Substance ID: DTXSID80977529
• Wikidata: Q76309837
• ChEMBL ID: CHEMBL607348
• Mol file: 6199-38-8.mol

Synonyms:6199-38-8;4,14-Dihydroxy-3-methoxy-N-methyl-6-oxomorphinan;BRN 0102261;RAM-322;Morphinan, 4,14-dihydroxy-3-methoxy-N-methyl-6-oxo-;Morphinan-6-one, 4,14-dihydroxy-3-methoxy-17-methyl-;(1R,9R,10S)-3,10-dihydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one;4,14-Dihydroxy-3-methoxy-17-methylmorphinan-6-one;CHEMBL607348;DTXSID80977529;LS-92133

Chemical Property of 4,14-Dihydroxy-3-methoxy-N-methyl-6-oxomorphinan

Chemical Property:

• Vapor Pressure: 3.44E-11mmHg at 25°C
• Melting Point: 142-145 °C
• Boiling Point: 509.2°C at 760 mmHg
• PKA: 9.73±0.40(Predicted)
• Flash Point: 261.7°C
• Density: 1.35g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 317.16270821
• Heavy Atom Count: 23
• Complexity: 511

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23CC(=O)CCC2(C1CC4=C3C(=C(C=C4)OC)O)O
• Isomeric SMILES: CN1CC[C@]23CC(=O)CC[C@]2([C@H]1CC4=C3C(=C(C=C4)OC)O)O
• Uses: Intermediate in the preparation of morphine alkaloids.

Technology Process of 4,14-Dihydroxy-3-methoxy-N-methyl-6-oxomorphinan

There total 14 articles about 4,14-Dihydroxy-3-methoxy-N-methyl-6-oxomorphinan 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: 90.0%

Oxycodone (76-42-6) → 4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-one (6199-38-8)

Guidance literature:

With ammonium chloride; zinc; In methanol;

DOI:10.1016/j.bmcl.2009.06.093

Reference yield: 71.0%

oxycodone hydrochloride (124-90-3) → 4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-one (6199-38-8)

Guidance literature:

With hydrogenchloride; acetic acid; zinc; for 0.166667h; Heating;

DOI:10.1021/jm9807003

Reference yield: 67.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4,14β-dihydroxy-3-methoxynormorphinan-6-one → 4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-one (6199-38-8)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In acetic acid; at 20 ℃; for 22h;

DOI:10.1016/j.bmc.2008.02.082

upstream raw materials:

oxycodone hydrochloride

4,5-epoxy-14-hydroxy-3-methoxy-17-methyl-morphinan-6-one

sulfuric acid

ethanol

Downstream raw materials:

14-Hydroxy-dihydrothebainon-4-methylether

14-hydroxy-3-methoxy-17-methyl-4-phenoxy-morphinan-6-one

Refernces

• 1、 Hupp, Christopher D.,Neumeyer, John L.. "Rapid access to morphinones: removal of 4,5-ether bridge with Pd-catalyzed triflate reduction". supporting information; experimental part. p. 2359 - 2361. Retrieved 2010/06/13.
• 2、 Nemoto, Toru,Fujii, Hideaki,Narita, Minoru,Miyoshi, Kan,Nakamura, Atsushi,Suzuki, Tsutomu,Nagase, Hiroshi. "Syntheses of 4,6′-epoxymorphinan derivatives and their pharmacologies". . p. 4304 - 4312. Retrieved 2008/12/20.