Practical oxirane ring opening with in situ prepared LiCN; synthesis of (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1 -butanenitrile

Article abstract of DOI:10.1080/00397919708007076

Trisubstituted oxirane 1 was regiospecifically opened with LiCN in situ prepared from acetone cyanohydrin and LiH to provide the corresponding β-hydroxy nitrile 2 in satisfactory yield, enabling us to manufacture a key intermediate for a new antifungal agent on a multi-kg scale. Some applications of this method to the ring opening of other oxiranes and nucleophilic substitution are also described.

Full text of DOI:10.1080/00397919708007076

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Synthetic Communications: An
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Practical Oxirane Ring Opening
with In Situ Prepared LiCN;
Synthesis of (2S,3R)-3-(2,4-
Difluorophenyl)-3-hydroxy-2-
methyl-4-(1H-1,2,4-triazol-1-
yl)-1-butanenitrile
a
a
Akihiko Tsuruoka , Shigeto Negi , Manabu
a
a
Yanagisawa & Kazumasa Nara
a
Toshihiko Naito, Norio Minami. Eisai Co. Ltd.,
Tsukuba Research Laboratories , 1—3 Tokodai 5
chome Tsukuba, Ibaraki, Japan , 300—26
Published online: 22 Aug 2006.
To cite this article: Akihiko Tsuruoka , Shigeto Negi , Manabu Yanagisawa &
Kazumasa Nara (1997) Practical Oxirane Ring Opening with In Situ Prepared LiCN;
Synthesis of (2S,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-
triazol-1-yl)-1-butanenitrile, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 27:20, 3547-3557, DOI:
10.1080/00397919708007076
To link to this article: http://dx.doi.org/10.1080/00397919708007076
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