RESEARCH ARTICLE

 

Synthesis of (S)-3-aminoethyl-1,2,3,4-tetrahydroisoquinoline (TIQ-diamine) via the Mitsunobu protocol*

 

 

Rahul B. Kawthekar^I; Byron K. Peters^I; Thavendran Govender^{II, **}; Hendrik G. Kruger^I; Glenn E.M. Maguire^I

^ISchool of Chemistry, University of KwaZulu-Natal, Durban, South Africa
^IISchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, 4000 South Africa
^IIISchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, 4000 South Africa

 

 

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ABSTRACT

The synthesis of (S)-3-Aminoethyl-1,2,3,4-tetrahydroisoquinoline (TIQ-diamine) was successfully achieved via the Mitsunobu protocol. The method from earlier reports utilizing aminolysis of commercially available TIQ-amino methyl ester, and reduction of the amide, proved to be inadequate for preparation of TIQ-diamines. The modified route requires three additional steps and consequently rendered three novel intermediates, which were furnished under mild conditions.

Keywords: Tetrahydroisoquinoline, TIQ-diamine, Mitsunobu reaction

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Acknowledgements

This work was supported by National Research Foundation (South Africa, GUN 2073251), SA/Swedish Research Links Programme grant and Aspen Pharmacare, SA.

 

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Received 7 July 2010
Revised 23 July 2010
Accepted 10 September 2010

 

 

* This paper was submitted upon invitation to invited speakers (CdK) at the South African Chemical Institute’s 11th Frank Warren Conference, January 2010, in Pietermaritzburg, KwaZulu-Natal, South Africa.
** To whom correspondence should be addressed. E-mail: govenderthav@ukzn.ac.za