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2-Azabicyclo[3.
3.
0]octane-3-carboxylic acid is an organic compound that is of great interest in the chemical industry due to its unique properties and potential applications.
This compound can be synthesized through several different routes, each with its own advantages and disadvantages.
In this article, we will explore the most commonly used synthetic routes for 2-Azabicyclo[3.
3.
0]octane-3-carboxylic acid and discuss their benefits and drawbacks.
Route 1: via Abetaloxime
The first synthetic route for 2-Azabicyclo[3.
3.
0]octane-3-carboxylic acid involves the synthesis of abetaloxime, which is then converted into the desired acid.
This route is widely used due to its simple and efficient synthesis process.
The synthesis of abetaloxime begins with the reaction of o-phenylendiamine with chloroform in the presence of a strong acid catalyst, such as sulfuric acid.
This reaction leads to the formation of N-chloro-o-phenylendiamine, which is then nitrated with nitrating acid, such as nitric acid, in the presence of a solvent, such as acetonitrile.
The resulting nitro compound is then reacted with an aminoalcohol, such as meglumine, to form abetaloxime.
Once the abetaloxime has been synthesized, it can be converted into 2-Azabicyclo[3.
3.
0]octane-3-carboxylic acid through a series of chemical reactions.
This conversion involves the reduction of the nitro group in abetaloxime using a reducing agent, such as hydrogen in the presence of a metal catalyst, such as palladium on barium oxide.
The reduction reaction leads to the formation of the corresponding amide, which is then hydrolyzed in a basic medium to yield the desired acid.
Advantages:
The synthetic route via abetaloxime is simple, efficient, and well-established, making it a popular choice for industrial applications.
Disadvantages:
The synthesis of abetaloxime requires several steps, which can increase the cost and complexity of the process.
Additionally, the use of toxic reagents, such as nitrating acid, requires strict safety measures to prevent harm to workers.
Route 2: via N-Cbz-L-alanine
The second synthetic route for 2-Azabicyclo[3.
3.
0]octane-3-carboxylic acid involves the synthesis of N-Cbz-L-alanine, which is then converted into the desired acid.
This route is commonly used due to its high yield and ease of operation.
The synthesis of N-Cbz-L-alanine begins with the condensation of L-alanine with chloromethylphenyl imine in the presence of a coupling agent, such as dicyclohexylcarbodiimide (DCC).
The resulting compound is then nitrated with nitrating acid, such as nitric acid, in the presence of a solvent, such as acetonitrile.
The resulting nitro compound is then reduced using a reducing agent, such as lithium aluminum hydride (LAH), to form the corresponding amine.
Once the N-Cbz-L-alanine has been synthesized, it can be converted into 2-Azabicyclo[3.
3.
0]octane-3-carboxylic acid through a series of chemical reactions.
This conversion involves the hydrolysis of theCBZ (carbobenzyloxy) group in N-Cbz-L-alanine using a strong acid, such as hydrochloric acid, followed by the reduction of the resulting aldehyde using a reducing agent, such as lithium aluminum hydride (LAH).
Advantages:
The synthetic route via N-Cbz-L-alanine is highly yielding and easy to operate, making it a popular choice for industrial applications.
Disadvantages:
