22152-80-3

Basic information

• Product Name: [5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol
• CAS NO: 22152-80-3
• Molecular Weight: 441.611
• Mol File: 22152-80-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: [5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol(22152-80-3)
• EPA Substance Registry System: [5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol(22152-80-3)

Safety Data

• Hazardous Substances Data: 22152-80-3(Hazardous Substances Data)

Upstream product

• 15358-23-3 (5α,7β)-4,5-epoxy-17-methyl-3,6-dimethoxy-7β-acetyl-6,14-ethenomorphinan 
• 507-20-0 tertiary butyl chloride 
• 16196-83-1 7α-acetyl-6,14-endoethanotetrahydrothebaine 
• 16196-82-0 7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine 
• 115-37-7 thebaine 
• 677-22-5 tert-butylmagnesium chloride 
• 15358-22-2 thevinone 
• 13965-70-3 4,5α-epoxy-6α,14α-etheno-7α-(1-hydroxy-1,2,2-trimethylpropyl)-3,6β-dimethoxy-17-methylmorphinan 

Downstream Products

• 136232-95-6 buprenorphine hydrochloride 
• 84712-92-5 (2S)-2-[(5R,6R,7R,14S)-N-cyclopropanoyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol 
• 78715-23-8 norbuprenorphine 
• 52485-79-7 Buprenorphine 
• 22151-78-6 (S)-2-((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol 

Relevant articles and documents

PROCESS FOR THE SYNTHESIS OF BUPRENORPHINE

The present invention relates to a novel route of synthesis for the opioid receptor antagonist Buprenorphine or a pharmaceutically acceptable salt thereof, starting from thebaine, wherein the route comprises the reaction of the baine with a dienophile; forming an alkylated reaction product by reaction with a Grignard-reagent; formation of an cyanamide; deprotection of the cyanamide- and the phenolic-oxygen-moiety, wherein the cleavage of one or both groups is performed in the presence of an alkali or alkaline earth sulfide; followed by derivatization with a cyclopropyl-halogen and hydrogenation to yield Buprenorphine.

PROCESS FOR THE PREPARATION OF (S)-2-((4R,4AS, 6R,7AR,12BS)-7,9-DIMETHOXY-1,2,3,4,5,6,7,7A-OCTAHYDRO-4A,7-ETHANO-4, 12-METHANOBENZOFURO[3,2-E] ISOQUINOLIN-6-YL)-3,3-DIMETHYLBUTAN-2-OL

An invention includes a process for the preparation of (S)-2((4R,4aS,6R,7R,7aR,12bS)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol.

INDUSTRIAL PROCESS FOR THE PREPARATION OF BUPRENORPHINE AND ITS INTERMEDIATES

There is provided an efficient industrial process for the preparation of 21-cyclopropyl-7α-(2-hydroxy-3,3-dimethyl-2-butyl)-6,14-endo-ethano-6,7,8,14-tetrahydro-oripavine, i.e. buprenorphine of Formula-I in high yield and purity, with enhanced safety and eco-friendly norms. The invention further relates to an improved process for preparation of intermediates thereof in high yield and purity.