Journal of Labelled Compounds and Radiopharmaceuticals 2014-05-15

Synthesis of isotopically labeled 1,3-dithiane.

Rodolfo A Martinez, David R Glass, Erick G Ortiz, Marc A Alvarez, Clifford J Unkefer

Index: J. Labelled Comp. Radiopharm. 57(5) , 338-41, (2014)

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Abstract

The 1,3-dithiane is a protected formaldehyde anion equivalent that could serve as a useful labeled synthon. We report a facile synthesis of 1,3-[2-(13)C]- and 1,3-[2-(13)C, 2-(2)H2]dithiane in two steps from [(13)C]- or [(13) C, (2)H3 ]methyl phenyl sulfoxide. We have previously reported the high yield synthesis of [(13)C]methyl phenyl sulfide from [(13)C]MEOH and the oxidation of [(13)C]methyl phenyl sulfide to [(13)C]methyl phenyl sulfoxide. Here, we describe the facile exchange of deuterium from (2) H2 O into [(13)C]methyl phenyl sulfoxide to yield [(13)C, (2)H3]methyl phenyl sulfoxide. Thus, from [(13)C]MEOH and (2)H2O, all possible C2 stable isotopomers of 1,3-dithiane are available. Our synthetic route is also amenable to preparation of radiolabeled 1,3-dithianes.Copyright © 2014 John Wiley & Sons, Ltd.