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Synthesis of (R)‐(2,3,4,5,6‐pentadeuterophenyl)oxirane
Author(s) -
Matthews Lee,
Ellis Martin K,
Cullis Paul N,
Farmer Peter B
Publication year - 1997
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(199706)39:6<479::aid-jlcr993>3.0.co;2-6
Subject(s) - chemistry , lithium aluminium hydride , potassium hydroxide , yield (engineering) , benzene , lithium (medication) , diol , friedel–crafts reaction , organic chemistry , medicinal chemistry , acylation , mandelic acid , hydroxide , lithium hydroxide , catalysis , ion , ion exchange , medicine , materials science , metallurgy , endocrinology
Abstract (R)‐(2,3,4,5,6‐Pentadeuterophenyl)oxirane, 5 was synthesized with an overall yield of 6.3% from benzene‐d 6 . Friedel‐Crafts acylation of benzene‐d 6 with methyl oxalylchloride gave methyl 2‐oxo‐2‐(2,3,4,5,6‐pentadeuterophenyl)acetate, 1 that was chirally reduced ( Saccharomyces cerevisiae ) to methyl (R)‐2‐hydroxy‐2‐(2,3,4,5,6‐pentadeuterophenyl)acetate (methyl (R)‐d 5 ‐mandelic acid), 2 . Reduction of 2 with lithium aluminium hydride gave (R)‐(2,3,4,5,6‐pentadeuterophenyl)ethane‐1,2‐diol, 3 . Tosylation of 3 and subsequent treatment with potassium hydroxide assisted cyclisation to 5 . © 1997 John Wiley & Sons, Ltd.