Intermediates to 4-amino-hexahydrobenz[cd]indoles and processes therefor
AssigneeEli Lilly and Company
InventorsThomas J. Kress, M. Robert Leanna, Michael J. Martinelli, Barry C. Peterson
Life of this patent
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Abstract
New intermediates, and processes therefor, provide an efficient method for deriving 4-amino-1,2,-2a,3,4,5-hexahydrobenz[cd]indoles, which are themselves intermediates to useful CNS agents, from the Kornfeld-Woodward ketone and like compounds. Preferred embodiments provide means for the preparation of substantially pure enantiomers of the desired 4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indole.
Claims6
A stereospecific process for preparing a substantially pure enantiomer of the compound of the formula ##STR10## wherein i) the 2-carbon is in the R configuration, the 4 carbon is in the R configuration, the 5 carbon is in the R configuration;
- and the carbon marked * is in the S configuration;
- or
- ii) the 2-a carbon is in the S configuration, the 4 carbon is in the S configuration, the 5 carbon is in the S configuration, and the carbon marked * is in the R configuration;
- or
- iii) the 2-a carbon is in the R configuration, the 4 carbon is in the S configuration, the 5 carbon is in the S configuration, and the carbon marked * is in the R configuration;
- or
- iv) the 2-a carbon is in the S configuration , the 4 carbon is in the configuration, the 5 carbon is in the R configuration, and the carbon marked * is in the S configuration;
- which process comprises:
- 1) reaction of a mixture of substantially the .alpha.-isomers or substantially the .beta.-isomers of the compound of the formula ##STR11## with a substantially pure optical isomer of 1-phenylethylamine, in n-butanol, to form a mixture of enantiomers of said compound;
- 2) selective crystallization of one of said enantiomers;
- and
- 3) isolation of the crystallized enantiomer.
Dependencies are inferred from the claim text.