The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Aug. 30, 2011
Filed:
Jun. 08, 2007
Michael James Rishel, Rensselaer, NY (US);
Kande Kankananamalage Dayarathna Amarasinghe, Latham, NY (US);
Sean Richard Dinn, Delmar, NY (US);
Bruce Fletcher Johnson, Scotia, NY (US);
Michael James Rishel, Rensselaer, NY (US);
Kande Kankananamalage Dayarathna Amarasinghe, Latham, NY (US);
Sean Richard Dinn, Delmar, NY (US);
Bruce Fletcher Johnson, Scotia, NY (US);
General Electric Company, Niskayuna, NY (US);
Abstract
A method of preparing a tetrabenazine compound (TBZ compound) having structure I comprising the steps of reacting a nucleophilic alkenyl species with aldehyde compound II and oxidizing the resultant allylic alcohol to provide enone III. The protecting group Pon the tetrahydroisoquinoline nitrogen is removed and the resultant deprotected intermediate is induced to undergo an amino cyclization reaction to provide a product TBZ compound having structure I. The method may be used to prepare either enantiomeric form of tetrabenazine; (+)-tetrabenazine or (−)-tetrabenazine. Alternatively the method may be adapted to provide a mixture enriched in one tetrabenazine enantiomer, a racemic mixture, or a diastereomeric mixture of tetrabenazine compounds. In addition, the present invention provides novel synthetic intermediate compositions which may be used to prepare either or both enantiomers of tetrabenazine, derivatives of tetrabenazine, and analogs of tetrabenazine.