Published TCIMAIL newest issue No.198
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Multi-functional Chiral Building Blocks
No.118(January 2004)
- C1733
- (R)-4-Chloro-3-hydroxy-n-butyric Acid Ethyl Ester (1a) (*This product is discontinued.)
- C1717
- (S)-4-Chloro-3-hydroxy-n-butyric Acid Ethyl Ester (1b)

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
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