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ChemicalBook CAS DataBase List Tropinone
532-24-1

Tropinone synthesis

8synthesis methods
The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine.
The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%.
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Yield:532-24-1 70%

Reaction Conditions:

with sodium tetrafluoroborate;potassium hydroxide in acetone at 100; for 12 h;Inert atmosphere;Schlenk technique;Oppenauer Oxidation;

Steps:

3.8. General procedure for catalytic Oppenauer-type oxidation

General procedure: To a mixture of ruthenium complex (0.04 mmol), KOH (0.4 mmol) and NaBF 4 (0.16 mmol) were added acetone (2 mL) and a substrate (0.8 mmol), the resulting mixture was heated at reflux in argon for 12 h or 100 °C for 12 h with some inactive substrates ( Table 3 , 2o-2r ). After the reaction completed, the prod- uct was isolated by column chromatography on silica gel with dichloromethane-petroleum ether as eluents.

References:

Liu, Hongming;Luo, Shubiao;Xue, Peng;Zhou, Jun [Journal of Organometallic Chemistry,2022,vol. 965-966,art. no. 122323] Location in patent:supporting information

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