Enantiomeric separation of (RS)1-(4-chlorophenyl)-2-chloroethano

Details Enantiomeric separation of (RS)1-(4-chlorophenyl)-2-chloroethano Enantiomeric separation of (RS)1-(4-chlorophenyl)-2-chloroethano

1995-12-22

1997-10-14

Saucier, Sandra E.

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435156, 435874, 435921, C12P 4100

Patent

active

056771681

ABSTRACT:
Process for the preparation of one or both enantiomers of 1-(4-chlorophenyl)-2-chloroethanol, which comprises an enantioselective enzymatic hydrolysis of (.+-.)-.alpha.-(4-chlorophenyl)chloroethyl acetate by means of an enzyme which is horse liver acetone powder, lipase PS from Pseudomonas fluorescens, lipase AK from Pseudomonas or the lipase from Candida antarctica, to give a mixture of unhydrolysed R-(-)-.alpha.-(4-chlorophenyl)chloroethyl acetate and S-(+)-1-(4-chlorophenyl)-2-chloroethanol, and optional separation of R-(-)-.alpha.-(4-chlorophenyl)chloroethyl acetate and optional hydrolysis of it to give R-(-)-1-(4-chlorophenyl)-2-chloroethanol and use of the enantiomers of 1-(4-chlorophenyl)-2-chlorethanol for the preparation of the enantiomers of eliprodil and of their salts.

REFERENCES:
patent: 5312950 (1994-05-01), Boaz
Langrand G et al., Lipase Catalyzed Reactions and Strategy for Alcohol Resolution, Tet. Lett. 27:29-32 (1986).
Nieduzak, T.R. et al, "Multigram lipase-catalyzed enantiose-selective acylation in the synthesis of the four stereoisomers of a new biologically active alpha-aryl-4-piperidinemethanol derivative", Tetrahedron: Asymmetry, vol. 2, No. 2, 1991, pp. 113-122.
Kutsuki, H. et al, "Asymmetric hydrolysis of (d1)-1-acyloxy-2-halo-1-phenylethanes with lipase", Agric. Biol. Chem., vol. 50, No. 9, 1986, pp. 2369-2373.
Woodcock, D., "Insecticidal activity and chemical constitution Part I. Chlorinated p-chloroethylbenzene", Journal of the Chemical Society, 1949, pp. 203-207.

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