Method of preparing (R)-4-amino-3-hydroxybutyric acid

Details Method of preparing (R)-4-amino-3-hydroxybutyric acid Method of preparing (R)-4-amino-3-hydroxybutyric acid

1988-02-29

1989-12-12

Moyer, Donald B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

548532, 548544, C07C10130, C07D20712, C07D20724, C07D207273

Patent

active

048869082

ABSTRACT:
(R)-4-amino-3-hydroxybutyric acid is prepared from the hydrochloride of the methyl ester or ethyl ester of (2S, 4R)-4-hydroxyproline via the intermediary stages of the corresponding, non-isolated (R)-4-hydroxy-1-pyrroline-2-carboxylic acid ester and the isolated (R)-4-hydroxy-2-pyrrolidone. The (R)-4-amino-3-hydroxybutyric acid which is useful for pharmacological purposes is obtainable in a high yield according to this method.

REFERENCES:
Chem. Abstracts, vol. 108, No. 21 (1988), 187240s.
The Merck Index, Tenth Edition, 1983, pp. 64, 66, 257-258, Item 432, ".gamma.-Aminobutyric Acid"; item 447, 4-Amino-3-hydroxybutyric Acid; item 1833, Carnitine.
Rajashekhar, B. et al., "Synthesis of Enantiomerically Pure .gamma.-Amino-.beta.-hydroxybutyric Acid Using Malic Acid as the Chiral Precursor", J. Org. Chem. 1985 (50), pp. 5480-5484.
Hausler, J. "A Convenient Synthesis of (R)-.gamma.-Amino-.beta.-hydroxybutyric Acid (GABOB) from Natural (2S,4R)-4-Hydroxyproline", Monatsh. Chem. 1987, 118 (6-7), pp. 865-869 (English Translation).

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