A process for preparing an optically active cineole derivative
AssigneeBASF Agro B.V.
InventorsKlaus Ditrich, Michael Rack, Stefan Benson, Roland Goetz, Helmut Kraus
Life of this patent
Estimating the term…
Abstract
The present invention relates to a process for preparing optically active 1,4-cineole derivatives by enzymatic resolution and enantiomerically pure optically active 1,4-cineole derivatives of purity greater than 99.9% that have been prepared by this process. The present invention further relates to a process for preparing 7-oxabicyclo[2.2.1]heptane derivatives from the enantiomerically pure optically active 1,4-cineole derivatives.
Claims21
1-15. (canceled)
A process for preparing an optically active compound of formula (II-R),
- or an optically active compound of formula (II-S),
- wherein
- R1 is selected from the group consisting of hydrogen and unsubstituted or substituted alkyl and
- R2 is selected from the group consisting of hydrogen and unsubstituted or substituted alkyl;
- said process comprises at least the steps of:
- (i) reacting a mixture comprising a compound of formula (II)
- wherein R1 and R2 are as defined above, with an acylating agent in the presence of a hydrolase to obtain a mixture containing the first enantiomer of the compounds of formula (II) in acylated form and the second enantiomer of the compounds of formula (II) in unacylated form;
- and
- (ii) isolating the second enantiomer of the compound of formula (II) in unacylated form from the mixture of step (i) to obtain an optically active compound of formula (II-R) or an optically active compound of formula (II-S) and a mixture containing the first enantiomer of the compounds of formula (II) in acylated form.
An optically active compound of formula (IIa-R),
- or an optically active compound of formula (IIa-S),
- wherein,
- R1 is selected from the group consisting of hydrogen and unsubstituted or substituted alkyl;
- R2 is selected from the group consisting of hydrogen and unsubstituted or substituted alkyl;
- R3 is selected from the group consisting of hydrogen and —COOR′;
- wherein R′ is hydrogen or unsubstituted or substituted alkyl;
- and
- n is 1 to 16.
Dependencies are inferred from the claim text.