Process for the preparation of an optically active indoline-2-ca

Details Process for the preparation of an optically active indoline-2-ca Process for the preparation of an optically active indoline-2-ca

1999-02-12

2000-09-19

McKane, Joseph

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548492, 548493, 562473, 560 19, C07D20912, C07D20926

Patent

active

061214604

ABSTRACT:
Process for the preparation of an optically active N-acyl-indoline-2-carboxylic acid in which a mixture of enantiomers of N-acyl-indoline-carboxylic acid is contacted with an optically active resolving agent and the optically active N-acyl-indoline-2-carboxylic acid is liberated from the resulting diastereomeric salt, as resolving agent use being made of a compound of formula 1, where R.sub.1 represents an alkyl group and R.sub.2 a hetero-aryl group or where R.sub.1 and R.sub.2 together with the C atoms to which they are bound form a cycloalkyl group with 5-8 C atoms, fused with a hetero-aryl group. Preferably, a mixture of enantiomers of an N-acyl-indoline-2-carboxylic acid is prepared in a process comprising the steps of Fischer indole cyclization of a 2-phenylhydrazone propionic acid or a derivative thereof in the presence of an acid catalyst, if necessary hydrolysis of the derivative to the corresponding acid, acylation at the N-position and reduction of the indole compound to the corresponding indoline compound, after which the resulting N-acyl-indoline-2-carboxylic acid is subjected to the resolution. The 2-phenylhydrazonopropionic acid or a derivative thereof is preferably obtained from phenylhydrazine and pyruvic acid or the corresponding derivative thereof.

REFERENCES:
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patent: 4665087 (1987-05-01), Vlattas
patent: 4824964 (1989-04-01), Miyata et al.
patent: 5149821 (1992-09-01), Moore et al.
patent: 5166361 (1992-11-01), Zepp
Tsukamoto, Masatoshi et al., Abstract No. 60525w, "Optical Resolution of (RS)-1-Acetyl-2-Carboxylic Acid", Chemical Abstracts, Aug. 18, 1986, vol. 105, No. 7, Columbus, Ohio, US.

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