Organic & Biomolecular Chemistry 2012-04-28

Radical-mediated nitrile translocation as the key step in the stereoselective transformation of 2-(4-chloro-2-cyanobutyl)aziridines to methyl cis-(1-arylmethyl-4-phenylpiperidin-2-yl)acetates.

Karel Vervisch, Matthias D'hooghe, Karl W Törnroos, Norbert De Kimpe

Index: Org. Biomol. Chem. 10(16) , 3308-14, (2012)

Full Text: HTML

Abstract

Non-activated 2-(4-chloro-2-cyano-2-phenylbutyl)aziridines were used as building blocks for the stereoselective synthesis of novel cis-2-cyanomethyl-4-phenylpiperidines via a microwave-assisted aziridine to piperidine ring expansion followed by a radical-induced nitrile translocation through initial formation and subsequent cleavage of intermediate bicyclic iminyl radicals. Furthermore, these 2-(cyanomethyl)piperidines were shown to be eligible substrates for the preparation of methyl cis-(1-arylmethyl-4-piperidin-2-yl)acetates through a Pinner reaction using gaseous HCl in methanol.This journal is © The Royal Society of Chemistry 2012

Related Compounds

  • 4-Phenylpiperidine

Related Articles:

A strategy for isotope containment during radiosynthesis--devolatilisation of bromobenzene by fluorous-tagging-Ir-catalysed borylation en route to the 4-phenylpiperidine pharmacophore.

2008-11-21

[Org. Biomol. Chem. 6 , 4093-4095, (2008)]

Structure-activity studies of morphine fragments. I. 4-alkyl-4-(m-hydroxy-phenyl)-piperidines.

1988-09-01

[Mol. Pharmacol. 34(3) , 363-76, (1988)]

Clandestine drug synthesis.

1986-01-01

[Med. Res. Rev. 6(1) , 41-74, (1986)]

Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.

1991-12-01

[J. Med. Chem. 34(12) , 3360-5, (1991)]

Influence of cocaine history on the behavioral effects of Dopamine D(3) receptor-selective compounds in monkeys.

[Biol. Psychiatry 36(5) , 1104-13, (2011)]

More Articles...