ChemicalBook CAS DataBase List Tropinone

Tropinone synthesis

8synthesis methods

Product Name:Tropinone
CAS Number:532-24-1
Molecular formula:C8H13NO
Molecular Weight:139.19

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%.

911648-75-4
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532-24-1
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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

120-29-6 Synthesis

120-29-6
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532-24-1
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References

1192-93-4
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593-51-1 Synthesis

593-51-1
526 suppliers
$21.00/100g

532-24-1
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References

8-Azabicyclo[3.2.1]octane-2,4-dicarboxylic acid, 8-methyl-3-oxo-, 2,4-dimethyl ester

100371-46-8
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36127-17-0 Synthesis

36127-17-0
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532-24-1
388 suppliers
$9.00/10g

References

502-41-0 Synthesis

502-41-0
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532-24-1
388 suppliers
$9.00/10g

References

Tropinone Related Search:

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