Process for the reduction of amino acids and the derivatives the

Details Process for the reduction of amino acids and the derivatives the Process for the reduction of amino acids and the derivatives the

1997-03-03

1998-04-28

McKane, Joseph

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562433, 562445, 562452, C07D26324

Patent

active

057446113

DESCRIPTION:

BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority from German application No. 4431529.5 filed Sep. 3, 1994 and PCT/EP95/03281 filed Aug. 17, 1995, the subject matter of which is hereby incorporated herein by reference.


FIELD OF THE INVENTION

The present invention relates to a process for the reduction of amino acids of the formula I ##STR2## in which n equals 0 or 1, identical or different and mean H, aryl, alkyl or arylalkyl, wherein in the latter two cases the carbon chain may be substituted and/or interrupted by heteroatoms such as N, O or S or groups containing such atoms, different and mean arylalkyloxycarbonyl, alkyloxycarbonyl or oxycarbonyl, identical or different and mean acylaminoalkyl or hydroxyl, R.sup.2, to yield the corresponding amino alcohols of the formula II ##STR3## in which R.sup.1 to R.sup.6 and n have the meaning stated for the formula I, first step in at least one linear or branched-chain alcohol having 1-5 C atoms with the addition of acid and with heating to yield an ester, wherein a reaction mixture containing the ester is obtained and the ester is reduced in a second step with alkali metal or alkaline earth metal borohydride to yield compounds of the formula II.
In the event that one of the residues R.sup.3, R.sup.4, R.sup.5 or R.sup.6 in the compounds of the type of formulae I, II forms a ring with one of the residues R.sup.1 or R.sup.2, it is understood that the name of both the residues involved in forming the ring will change in accordance with the rules of chemical nomenclature. Thus, if ring formation does occur, the corresponding residues R.sup.1 to R.sup.6 actually involved in forming the ring will be termed either alkylene or arylalkylene, wherein the carbon chain or ring thereof may be substituted by heteroatoms such as N, O and/or S or groups containing such atoms and/or interrupted by heteroatoms such as N, O and/or S, while R.sup.1 and R.sup.2 may, however, also be carbonyl, arylalkyleneoxycarbonyl, alkyleneoxycarbonyl or oxycarbonyl and R.sup.3, R.sup.4, R.sup.5 or R.sup.6 may be arylene, acylaminoalkylene or oxygen. As stated, these names should be used only for those residues actually attached to the ring. Otherwise, the generally stated names apply to those residues not involved in ring closure.
The amino alcohols obtainable by reducing amino acids or amino acid derivatives are versatile components for synthesis. In particular, the corresponding chiral compounds are important components, for example for preparing optically active compounds.


BACKGROUND OF THE INVENTION

A review of amino alcohols may be found in G. M. Coppola and H. F. Schuster, Asymmetric Synthesis, John Wiley & Sons, New York 1987; or in M. Nogradi, Stereoselective Synthesis, Verlag Chemie, Weinheim 1987.
The amino alcohols may thus be used to produce chiral catalysts, with which enantioselective cyclopropanations, reductions, hydrosilylations, Diels-Alder reactions and other reactions may be performed. This topic is reviewed in C. Bolm, Angew. Chem. 1991, 103, 556. The amino alcohols are frequently incorporated into important synthesis intermediates in order to induce the formation of centres of asymmetry in subsequent reactions by the action of steric or electronic influences, wherein the degrees of enantio- or diastereoselectivity are frequently extraordinarily high. Examples which may be mentioned are 4-substituted oxazolidin-2-ones (J. R. Gage, D. A. Evans, Org. Synth. 1989, 68, 77 and the literature cited therein) and bicyclic lactams (D. Romo, A. I. Meyers, Tetrahedron 1991, 47, 9503).
Amino alcohols may also be integrated into peptide isosteres, wherein products having elevated physiological activity may be obtained, for example enkephalin analogues having a stronger and longer lasting analgesic action (Y. Kiso, M. Yamaguchi, T. Akita, H. Moritoki, M. Takei, H. Nakamura, Naturwissenschaften 1981, 68, 210; J. Pless, W. Bauer, F. Cardinaux, A. Closse, D. Hauser, R. Huguenin, D. Roemer, H. H. Buescher, inhibitors (for example T. F. Tam, J. Carriere, I. D. MacDon

REFERENCES:
Bull. Chem. Soc. Japan, vol. 57, pp. 2327-2328, Soai et al., 1984.
CA 101: 152278p Novel procedure . . . ester. Soai et al., 1984.

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