54186-43-5

Basic information

• Product Name: N-(3-methoxyphenylethyl)-(3,5-dibenzyloxy-4-methoxyphenyl)acetamide
• CAS NO: 54186-43-5
• Molecular Weight: 511.618
• Mol File: 54186-43-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(3-methoxyphenylethyl)-(3,5-dibenzyloxy-4-methoxyphenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-methoxyphenylethyl)-(3,5-dibenzyloxy-4-methoxyphenyl)acetamide(54186-43-5)
• EPA Substance Registry System: N-(3-methoxyphenylethyl)-(3,5-dibenzyloxy-4-methoxyphenyl)acetamide(54186-43-5)

Safety Data

• Hazardous Substances Data: 54186-43-5(Hazardous Substances Data)

Upstream product

• 83553-80-4 3,5-Di-O-acetylgallussaeuremethylester 
• 100-39-0 benzyl bromide 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 13089-97-9 methyl 3,5-diacetoxy-4-methoxy benzoate 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 99-24-1 methyl galloate 
• 24093-82-1 3,5-bis(benzyloxy)-4-methoxybenzyl chloride 
• 27229-56-7 [3,5-bis(benzyloxy)-4-methoxyphenyl]methanol 
• 54186-41-3 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 54186-42-4 2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetic acid 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 

Relevant articles and documents

Chemistry of opium alkaloids, 45. Improvements in the total synthesis of morphine

The chiral 1,2,3,4-tetrahydroisoquinoline intermediates in the Price and Beyerman routes to morphine, (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy- 1,2,3,4-tetrahydroisoquinoline (6) and (+)-(R)-1-(3,5-dibenzyloxy-4- methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (5), were prepared in high ee by ruthenium-catalyzed asymmetric transfer hydrogenation of the corresponding imine precursors (Noyori method). The yield of the key raw material in the Beyerman route, 3,5-dibenzyloxy-4-methoxyphenylacetric acid (1), starting from gallic acid methyl ester (7) was improved by a factor of 5 over previously described syntheses. Key steps in the new procedure are the selective formation of methyl 3,5-dihydroxy-4-methoxybenzoate (9) via the 3,5-diacetate and an improved benzylation of the hydroxyl groups in 9.