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Synthesis of Tropine-Labeled Atropine I

1967; Elsevier BV; Volume: 56; Issue: 2 Linguagem: Inglês

10.1002/jps.2600560213

1520-6017

G Schmidt, Thomas E. Eling, John C. Drach,

Inorganic and Organometallic Chemistry

Yields for each step in the esterification of tropine and tropic acid have been determined with micro and semimicro quantities of reactants. In a similar way, the Robinson condensation has been studied. Data are compared with the findings of other investigators. In the esterification of micro quantities of tropine and tropic acid, 70–75 per cent of theoretical atropine yields are obtained routinely. Based on any intermediate in the Robinson condensation, micro quantities of reactants routinely produce 67–72 per cent of theoretical tropine yields. Predicted yields of 47–54 per cent atropine from Robinson intermediates were confirmed by synthesis of atropine from each of the Robinson reactants. The procedures are designed for the synthesis of labeled tropine and tropine-labeled atropine from labeled arabinose. Yields for each step in the esterification of tropine and tropic acid have been determined with micro and semimicro quantities of reactants. In a similar way, the Robinson condensation has been studied. Data are compared with the findings of other investigators. In the esterification of micro quantities of tropine and tropic acid, 70–75 per cent of theoretical atropine yields are obtained routinely. Based on any intermediate in the Robinson condensation, micro quantities of reactants routinely produce 67–72 per cent of theoretical tropine yields. Predicted yields of 47–54 per cent atropine from Robinson intermediates were confirmed by synthesis of atropine from each of the Robinson reactants. The procedures are designed for the synthesis of labeled tropine and tropine-labeled atropine from labeled arabinose.