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Synthesis of isotopically labeled 1,3‐dithiane
Author(s) -
Martinez Rodolfo A.,
Glass David R.,
Ortiz Erick G.,
Alvarez Marc A.,
Unkefer Clifford J.
Publication year - 2014
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3185
Subject(s) - chemistry , dithiane , sulfoxide , synthon , yield (engineering) , sulfone , medicinal chemistry , sulfide , stereochemistry , organic chemistry , materials science , metallurgy
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 H 2 ]dithiane in two steps from [ 13 C]‐ or [ 13 C, 2 H 3 ]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 H 2 O into [ 13 C]methyl phenyl sulfoxide to yield [ 13 C, 2 H 3 ]methyl phenyl sulfoxide. Thus, from [ 13 C]MEOH and 2 H 2 O, 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.