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Synthesis of 13 C‐enriched pyrrole from 2‐ 13 C d ‐galactose
Author(s) -
Williams Sean R.,
Maynard Heather D.,
Chmelka Bradley F.
Publication year - 1999
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/(sici)1099-1344(199910)42:10<927::aid-jlcr249>3.0.co;2-j
Subject(s) - chemistry , pyrrole , ammonium hydroxide , yield (engineering) , ammonium , pyranose , galactose , organic chemistry , sugar , metallurgy , materials science
The synthesis of 13 C‐enriched pyrrole, labeled adjacent to the nitrogen atom, is described. A convenient and effective bench‐top synthesis is given which uses a readily available enriched pyranose sugar, 2‐ 13 C d ‐galactose, as the starting material. In the first step of the synthesis, d ‐galactose is oxidized to produce mucic acid in 70–75% yield. Mucic acid is then treated with ammonium hydroxide to give ammonium mucate in 99% yield. In the final step, ammonium mucate is pyrolyzed to form pyrrole with a 35% yield. The pyrrole obtained in this manner is greater than 98% enriched at the α position. Copyright © 1999 John Wiley & Sons, Ltd.