Tetrahedron letters

A simple and efficient synthesis of 8-methyl-3, 8-diazabicyclo [3.2. 1] octane (azatropane) and 3-substituted azatropanes therefrom using pyroglutamic acid

…, N Sinha, A Mehta, F Naqvi, AK Agarwal, N Anand

Index: Singh, Rakesh K.; Jain, Sanjay; Sinha, Neelima; Mehta, Anita; Naqvi, Fehmida; Agarwal, Ashok K.; Anand, Nitya Tetrahedron Letters, 2007 , vol. 48, # 4 p. 545 - 548

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Citation Number: 6

Abstract

8-Methyl-3, 8-diazabicyclo [3.2. 1] octane (3-azatropane) is synthesized efficiently from pyroglutamic acid making use of amide activation. The key step of the synthesis involves reduction and cyclization of a nitroenamine intermediate. Several 3-substituted analogues of this azatropane were also synthesized via this methodology and evaluated for their affinity at D2 and 5-HT2A receptors.