Process for producing optically active 2-alkoxycyclohexanol deri

Details Process for producing optically active 2-alkoxycyclohexanol deri Process for producing optically active 2-alkoxycyclohexanol deri

1997-06-13

1998-05-12

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing oxygen-containing organic compound

435195, 435196, 435197, 435280, 435829, 435874, 435921, 435931, C12P 762, C12P 4100, C12N 914

Patent

active

057503826

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to a process for producing an optically active 2-alkoxycyclohexanol derivative, and more particularly, to a process for producing an (S,S)-2-alkoxycyclohexanol.
2. Prior Art
It is known that optically active 2-alkoxycyclohexanol derivatives such as (S,S)-2-alkoxycyclohexanol are important synthetic intermediates in the productions of medicines and agricultural chemicals.
As a process for producing an optically active 2-alkoxycyclohexanol derivative, for example, the following methods have been investigated: 1 the process in which a carboxylic ester of a (.+-.)-trans-2-methoxycyclohexanol is hydrolyzed selectively in R-configuration in the presence of hydrolase to give a carboxylic ester of an (S,S)-2-alkoxycyclohexanol and an (R,R)-2-methoxycyclohexanol (Tetrahedron, 50 (35), 10521-30 (1994), Synthesis, 12, 1137-40 (1990), and J. Chem. Soc. Chem. Commun., 3, 148-50 (1989)), 2 the process in which a carboxylic ester of a (.+-.)-trans-2-methoxycyclohexanol is hydrolyzed selectively in S-configuration in the presence of hydrolase to give an (S,S)-2-methoxycyclohexanol and a carboxylic ester of an (R,R)-2-alkoxyhexanol (WO94/20634), and 3 the process for obtaining an (R,R)-2-methoxycyclohexanol by asymmetric hydroboration of 1-methoxycyclohexene (J. Org. Chem., 53 (9), 1903-7 (1988)).
Though the process 1 is highly stereoselective, the configuration of an optically active 2-alkoxycyclohexanol obtained is (R,R)-configuration and a further hydrolysis of the carboxylic ester of (S,S)-2-alkoxycyclohexanol produced must be carried out in order to obtain (S,S)-2-alkoxycyclohexanol.
Though (S,S)-2-alkoxycyclohexanol can be obtained through the process 2, this method is not sufficiently stereoselective and there are some problems in productive efficiency and economical efficiency.
A stereoselectivity of process 3 is low, and further, there are such problems as reagents used in this process are expensive and etc.


SUMMARY OF THE INVENTION

Taking an account of the above-mentioned circumstances, the object of the present invention is to provide a process for efficiently producing an (S,S)-2-alkoxycyclohexanol in a single step from a (.+-.)-trans-2-alkoxycyclohexanol which is inexpensive and easily available.
The gist of this invention is a process for producing an (S,S)-2-alkoxycyclohexanol which comprises treating a (.+-.)-trans-2-alkoxycyclohexanol which is expressed by the general formula (1); ##STR1## (wherein R.sup.1 represents a lower alkyl, an alkenyl, a cycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted aralkyl group) with a hydrolase originating in a microorganism which is capable of esterifying the R-isomer stereospecifically in the presence of an acyl donor under a condition that no hydrolysis occurs substantially to thereby give an (S,S)-2-alkoxycyclohexanol which is expressed by the general formula (2); ##STR2## (wherein R.sup.1 is the same as previously defined), and a carboxylic ester of an (R,R)-2-alkoxycyclohexanol which is expressed by the general formula (3) ##STR3## (wherein R.sup.1 is the same as previously defined and R.sup.2 represents a hydrogen, straight-chain or branched alkyl having 1 to 17 carbon atoms, or straight-chain or branched alkenyl group having 1 to 17 carbon atoms), and then taking up said (S,S)-2-alkoxycyclohexanol.


DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, the present invention is explained in more details.
A (.+-.)-trans-2-alkoxycyclohexanol which is used in this invention is a compound given in the above general formula (1). R.sup.1 in the above formula is not specially limited to but includes a lower alkyl group such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, sec-butyl and the like; an alkenyl group such as vinyl, allyl, isobutenyl and the like; a cycloalkyl group such as cyclohexyl, cyclopentyl and the like; a substituted or unsubstituted aryl group such as p-nitrophenyl, a phenyl and the like; and a substituted or unsubstitute

REFERENCES:
Bhattacharya et al "Indian Journal of Chemistry" vol. 31B, Dec. 1991, pp. 898-890.

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