Tropinone synthesis
- Product Name:Tropinone
- CAS Number:532-24-1
- Molecular formula:C8H13NO
- Molecular Weight:139.2
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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532-24-1
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