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DOI: 10.1055/s-2005-872081
Efficient Synthesis of N-Alkyl Tetrahydroisoquinolines by Reductive Amination
Publication History
Publication Date:
20 July 2005 (online)
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Abstract
An expedient access to diverse N-alkyl 1,2,3,4-tetrahydroisoquinolines is reported by reductive amination of aldehydes and ketones with tetrahydroisoquinoline (THIQ) in the presence of Ti(Oi-Pr)4 and NaBH4. The N-alkyl THIQ products were rapidly purified by flow-through catch and release technique using commercially available polymer-supported sulfonic acid, MP-TsOH columns.
Key Words
reductive amination - tetrahydroisoquinoline - Ti(Oi-Pr)4 - NaBH4 - polymer-supported sulfonic acid column
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References
The work was presented in part by: Kumpaty H. J., Bhattacharyya S.; 228th ACS National Meeting, Philadelphia; American Chemical Society: Washington, DC, August 2004; paper ORGN-701
13The macroporous polystyrene-supported sulfonic acid, MP-TsOH columns (part number: 800477-0050-C) were obtained from Argonaut Technologies.