Asymmetric route to spirotetracyclic (1S)-5′,11′-dihydro-3H-spiro[cyclopentane-1,10′-dibenzo[a,d]cyclohepten]-3-one derivatives |
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| Authors: | Massimo Gianotti Daniele AndreottiDavide Casotto Mario MattioliAnna Mingardi Francesca PavoneRoberto Profeta Filippo Valente |
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| Institution: | Neurosciences CEDD, GlaxoSmithKline, Medicines Research Centre, Via A. Fleming 4, 37135 Verona, Italy |
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| Abstract: | A new synthetic pathway to the final compound 1-(1S)-5’,11’-dihydrospirocyclopentane-1,10’-dibenzoa,d]cyclohepten]-3-yl]-3-azetidinecarboxylic acid (1) was set up. The two preparative chiral HPLC separations needed in the first route were successfully avoided and replaced by two diastereomeric crystallizations of intermediate compounds 5 and 10. |
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| Keywords: | Diazo-insertion Diastereomeric crystallization Spirotetracyclic compounds Sleep disorders Zwitterion |
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