Process for the preparation of the (-)-antipode of (E)-1-cyclohe

Details Process for the preparation of the (-)-antipode of (E)-1-cyclohe Process for the preparation of the (-)-antipode of (E)-1-cyclohe

1987-03-12

1989-02-28

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D24908

Patent

active

048087254

ABSTRACT:
A process for the preparation of the (-)-antipode of (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene of the formula ##STR1## which comprises reacting the (E)-isomer of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one of the formula ##STR2## (a) with boron hydride in the presence of an optically active proline derivative of the formula ##STR3## in which, R.sup.1 is alkyl, phenyl or benzyl, or
(b) with a complex borohydride in the presence of an acid addition salt of the optically active proline derivative, in the presence of a diluent at a temperature between about -70.degree. C. and +60.degree. C. The proline derivatives are also new and are produced from S-proline esters. The end product is a known plant growth regulant.

REFERENCES:
patent: 4592772 (1986-06-01), Kraatz et al.
patent: 4607108 (1986-08-01), Feyen et al.
Asami et al., "An Asymmetric Reduction of Prochirol, etc.", Heterocycles, 12, (1979), 499.
Chemical Pharm. Bull., 31, 837-851, (1983).

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