1416165-61-1

Basic information

• Product Name: (R)-2-(1-(2-methoxy-5-methylphenyl)-1-phenylbut-3-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: (R)-2-(1-(2-methoxy-5-methylphenyl)-1-phenylbut-3-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 1416165-61-1
• Molecular Weight: 378.319
• Mol File: 1416165-61-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-2-(1-(2-methoxy-5-methylphenyl)-1-phenylbut-3-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(1-(2-methoxy-5-methylphenyl)-1-phenylbut-3-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1416165-61-1)
• EPA Substance Registry System: (R)-2-(1-(2-methoxy-5-methylphenyl)-1-phenylbut-3-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1416165-61-1)

Safety Data

• Hazardous Substances Data: 1416165-61-1(Hazardous Substances Data)

Upstream product

• 1416165-60-0 (R)-1-(2-methoxy-5-methylphenyl)but-3-enyl diisopropylcarbamate 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 7083-19-4 2-methoxy-5-methylbenzaldehyde 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 

Downstream Products

• 1416165-62-2 (S)-1-(2-methoxy-5-methylphenyl)-1-phenylbut-3-en-1-ol 
• 1416165-63-3 (R)-1-methoxy-4-methyl-2-(1-phenylbut-3-enyl)benzene 
• 1416165-64-4 (R)-4-(2-methoxy-5-methylphenyl)-4-phenylbutan-1-ol 
• 1416165-65-5 (R)-3-(2-methoxy-5-methylphenyl)-3-phenylpropanal 
• 518360-71-9 (R)-N,N-diisopropyl-3-(2-methoxy-5-methylphenyl)-3-phenylpropan-1-amine 
• 124937-51-5 (R)-(+)-tolterodine 

Relevant articles and documents

Enantioselective synthesis of (R)-tolterodine using lithiation/borylation- protodeboronation methodology

The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation-protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.