128524-63-0

Basic information

• Product Name: (+)-8-O-methylaphanorphine
• CAS NO: 128524-63-0
• Molecular Weight: 217.311
• Mol File: 128524-63-0.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (+)-8-O-methylaphanorphine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-8-O-methylaphanorphine(128524-63-0)
• EPA Substance Registry System: (+)-8-O-methylaphanorphine(128524-63-0)

Safety Data

• Hazardous Substances Data: 128524-63-0(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 620163-18-0 (1R,4S)-1-methyl-8-methoxy-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 67-56-1 methanol 
• 359882-21-6 (1S,4R)-3-benzyloxycarbonyl-8-methoxy-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 1301725-78-9 (1R,4R)-N-benzoyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 1301725-76-7 (5R)-N-(benzoyl)-5-(4-methoxybenzyl)-3-methylpyrrol-idin-3-ol 
• 1301725-75-6 (5R)-N-(tert-butylsulfonyl)-5-(4-methoxybenzyl)-3-methylpyrrolidin-3-ol 
• 1301725-73-4 (2R)-N-(tert-butylsulfonyl)-1-(4-methoxyphenyl)-3-(2-methyloxiran-2-yl)propan-2-ylamine 
• 1301725-71-2 (4S,Rs)-N-(tert-butylsulfinyl)-5-(4-methoxyphenyl)-2-methylpent-1-en-4-amine 
• 178681-78-2 (R)-2-(3-Methoxy-phenyl)-2-methyl-pentanedioic acid 1-ethyl ester 5-methyl ester 

Downstream Products

• 118964-06-0 (-)-aphanorphine 

Relevant articles and documents

An enantioselective approach to (-)-aphanorphine featuring a stereoselective oxidative amidation

A formal enantioselective synthesis of (-)-aphanorphine (91% ee), that culminates with the preparation of (+)-O-methyl aphanorphine, was achieved. The methodology involves the diastereoselective synthesis of a key 3,5-disubstituted pyrrolidinone intermediate by the intramolecular oxidative amidation of a suitably functionalized α-hydroxy pentenoic acid derivative. A late-stage N-formyl protection, which functions as a latent N-methyl group, is utilized as a simple alternative to a protecting group switch and subsequent N-methylation strategy implemented in all other syntheses of aphanorphine related to the present approach. The Royal Society of Chemistry 2013.

An effective route to (-)-aphanorphine using D-tyrosine as a chiral building block

A stereoselective approach toward a naturally occurring alkaloid, (-)-aphanorphine, has been achieved via a series of reactions from Boc-D-tyrosine. Georg Thieme Verlag Stuttgart.

Cyclic sulfamidates as lactam precursors. An efficient asymmetric synthesis of (-)-aphanorphine

A short and efficient enantioselective synthesis of (-)-aphanorphine is described based on the use of a cyclic sulfamidate to provide a suitably functionalised lactam that allows for construction of the tricyclic 3-benzazepine scaffold. The Royal Society