56135-34-3

Upstream product

• 186581-53-3 diazomethane 
• 14097-42-8 5-Hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 67-56-1 methanol 
• 200396-67-4 5-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline 
• 74-88-4 methyl iodide 
• 102877-50-9 1,2,3,4-tetrahydro-5-hydroxy-isoquinoline 
• 216064-44-7 2-trifluoroacetyl-1,2,3,4-tetrahydro-5-isoquinolinol 
• 69062-43-7 2-methyl-5-nitro-1,2,3,4-tetrahydro-isoquinoline 
• 14097-41-7 5-amino-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 216064-46-9 5-(tetrahydropyran-2-yloxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin 
• 117885-40-2 5-methoxy-2-methyl-isoquinolinium; iodide 

Relevant academic research and scientific papers

A novel solid support for derivatization and subsequent N-alkylation of secondary amines: Preparation of N-alkylated 5- and 6-alkoxy-1,2,3,4-tetrahydroisoquinolines via Mitsunobu reaction

A hydroxymethylated polystyrene resin has been converted to its vinylsulfonylethyl ether (1) by DBU catalyzed addition of the hydroxy groups to divinyl sulfone. The support obtained was used to convert 5- and 6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinolines to a set of N-alkylated tetrahydroisoquinolines bearing various 5- and 6-alkoxy substituents (5a-m). The synthesis involved attachment of the starting material to the support by Michael addition, acid-catalyzed removal of the tetrahydropyranyl protection, Mitsunobu etherification, quaternarization with alkyl amines, and release in solution with diisopropylethylamine.