Application

No.118
Multi-functional Chiral Building Blocks
C1733 (R)-4-Chloro-3-hydroxy-n-butyric Acid Ethyl Ester (1a) 5g
C1717 (S)-4-Chloro-3-hydroxy-n-butyric Acid Ethyl Ester (1b) 5g

The multi-functionalized esters of n-butyric acid 1 are useful building blocks having three functional groups, each with different reactivity in the neighborhood of a chiral carbon atom. A variety of optically active substances can be synthesized by employing each functionality. For example, 1 can be converted to tetrahydrofuranone 2 by treatment with hydrochloric acid, pyrrolidinone 3 by treatment with ammonium hydroxide, and tetrahydrofuran 4 by treatment with hydrochloric acid after reducing to alcohol. Oxazolidinone 5 can also be obtained via hydrazide. Furthermore, the esters 1 are employed for the synthesis of the important bioactive substance 4-amino-3-hydroxybutyric acid (GABOB) 6 and carnitine 7.

References

1) Synthesis of optically active heterocyclic compounds
a) Y. Yuasa, H. Tsuruta, Liebigs Ann./Recueil, 1997, 1877; b) R. Pellegata, I.
Dosi, M. Villa, G. Lesma, G. Palmisano, Tetrahedron, 41, 5607 (1985); c) M.
Bertau, M. Buli, E. Hungerbuler, P. Wagner, Tetrahedron: Asymmetry, 12,
2103 (2001).
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