US 4,072,698 AGranted

Resolution of aminonitriles

AssigneeThe Upjohn Company

InventorsThomas A. Hylton, Francis L. Shenton

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Abstract

The present invention is a chemical method for obtaining an optically pure 2-aminonitrile or a 2-aminoamide from (1) an optically impure mixture, (2) a racemic mixture, or (3) the optically pure enantiomer of the opposite configuration, in an amount greater than actually present, by use of optically active acids with a ketone or an aldehyde catalyst. Yields of greater than 70 percent of one enantiomer are obtained from racemic mixtures in very short time periods.

Claims37

Dependent claims

A process for producing an optically pure 2-aminonitrile enantiomer of the formula:

##STR11## where R is alkyl of 1 thru 6 carbon atoms;
cycloalkyl of 3 thru 6 carbon atoms;
aromatic of 6 thru 10 carbon atoms, substituted with 0 thru 3 substituents, which may be the same or different and are selected from the group consisting of alkyl of 1 thru 6 carbon atoms, hydroxyl, alkoxy where the alkyl group contains 1 thru 6 carbon atoms, cyclic alkylenedioxy where the alkylene group contains 1 thru 3 carbon atoms, halogen, trifluoromethyl, and cyano;
aralkyl of 7 or 8 carbon atoms substituted with 0 thru 3 substituents, which may be the same or different and are selected from the group consisting of alkyl of 1 thru 6 carbon atoms, hydroxyl, alkoxy where the alkyl group contains 1 thru 6 carbon atoms, or cyclic alkylenedioxy where the alkylene group contains 1 thru 3 carbon atoms;
2- or 3-furyl, 2- or 3-thienyl and 2- or 3-indolylmethyl in acid salt form in an amount greater than present in an optically impure 2-aminonitrile (III) mixture which comprises contacting the optically impure 2-aminonitrile (III) mixture with an optically active acid in the presence of a compound of the formula R.sub.1 COR.sub.2 (IV), the methyl or ethyl actal, ketal, hemiacetal, or hemi-ketal thereof, where R.sub.1 and R.sub.2 may be the same or different with the proviso that both R.sub.1 and R.sub.2 cannot both be aromatic and where R.sub.1 is alkyl of 1 thru 6 carbon atoms;
cycloalkyl of 4 thru 6 carbon atoms;
aromatic of 6 thru 10 carbon atoms, substituted with 0 thru 3 substituents selected from the group consisting of alkyl of 1 thru 6 carbon atoms, halogen, alkoxy where the alkyl group contains 1 thru 6 carbon atoms;
or aralkyl of 7 or 8 carbon atoms;
R.sub.2 is hydrogen or R.sub.1 ;
and when R.sub.2 is not hydrogen, R.sub.1 and R.sub.2 taken together with the attached carbon atom may form a cyclic ketone selected from the group consisting of cyclobutanone, cyclopentanone, cyclohexanone and cycloheptanone, and separating the diastereomeric acid salt of the optically pure 2-aminonitrile (III) enantiomer.

7 more elements

Dependencies are inferred from the claim text.

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Abstract

A process for producing an optically pure 2-aminonitrile enantiomer of the formula:

##STR11## where R is alkyl of 1 thru 6 carbon atoms;
cycloalkyl of 3 thru 6 carbon atoms;
aromatic of 6 thru 10 carbon atoms, substituted with 0 thru 3 substituents, which may be the same or different and are selected from the group consisting of alkyl of 1 thru 6 carbon atoms, hydroxyl, alkoxy where the alkyl group contains 1 thru 6 carbon atoms, cyclic alkylenedioxy where the alkylene group contains 1 thru 3 carbon atoms, halogen, trifluoromethyl, and cyano;
aralkyl of 7 or 8 carbon atoms substituted with 0 thru 3 substituents, which may be the same or different and are selected from the group consisting of alkyl of 1 thru 6 carbon atoms, hydroxyl, alkoxy where the alkyl group contains 1 thru 6 carbon atoms, or cyclic alkylenedioxy where the alkylene group contains 1 thru 3 carbon atoms;
2- or 3-furyl, 2- or 3-thienyl and 2- or 3-indolylmethyl in acid salt form in an amount greater than present in an optically impure 2-aminonitrile (III) mixture which comprises contacting the optically impure 2-aminonitrile (III) mixture with an optically active acid in the presence of a compound of the formula R.sub.1 COR.sub.2 (IV), the methyl or ethyl actal, ketal, hemiacetal, or hemi-ketal thereof, where R.sub.1 and R.sub.2 may be the same or different with the proviso that both R.sub.1 and R.sub.2 cannot both be aromatic and where R.sub.1 is alkyl of 1 thru 6 carbon atoms;
cycloalkyl of 4 thru 6 carbon atoms;
aromatic of 6 thru 10 carbon atoms, substituted with 0 thru 3 substituents selected from the group consisting of alkyl of 1 thru 6 carbon atoms, halogen, alkoxy where the alkyl group contains 1 thru 6 carbon atoms;
or aralkyl of 7 or 8 carbon atoms;
R.sub.2 is hydrogen or R.sub.1 ;
and when R.sub.2 is not hydrogen, R.sub.1 and R.sub.2 taken together with the attached carbon atom may form a cyclic ketone selected from the group consisting of cyclobutanone, cyclopentanone, cyclohexanone and cycloheptanone, and separating the diastereomeric acid salt of the optically pure 2-aminonitrile (III) enantiomer.

7 more elements