The Production Process of 1,1-Dimethylethyl (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

1,1-Dimethylethyl (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.
2.
1]heptane-2-carboxylate is an organic compound that is used as an intermediate in the production of various chemicals and pharmaceuticals.
The compound is synthesized through a multi-step process that involves several chemical reactions and purification steps.
This article provides an overview of the production process of 1,1-dimethylethyl (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.
2.
1]heptane-2-carboxylate.

Step 1: Preparation of Benzimidazole

The synthesis of 1,1-dimethylethyl (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.
2.
1]heptane-2-carboxylate begins with the preparation of benzimidazole, which is a key intermediate.
Benzimidazole is synthesized by reacting phthalic anhydride with sodium hydroxide and benzene in the presence of a catalyst, such as sulfuric acid.
The reaction produces a mixture of benzimidazole and its isomers, which are subsequently separated and purified.

Step 2: Coupling of Benzimidazole with Ethyl Bromide

The next step in the synthesis of 1,1-dimethylethyl (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.
2.
1]heptane-2-carboxylate involves the coupling of benzimidazole with ethyl bromide in the presence of a solvent, such as ether or hexane.
The reaction is typically carried out under anhydrous conditions and in the presence of a catalyst, such as aluminum chloride or ferric chloride.
This reaction results in the formation of a new compound, which is then purified to remove any impurities.

Step 3: Condensation Reaction with Isonicotinic Acid Hydrazide

The next step in the synthesis of 1,1-dimethylethyl (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.
2.
1]heptane-2-carboxylate is a condensation reaction with isonicotinic acid hydrazide.
This reaction is typically carried out in the presence of a solvent, such as ethanol or methanol, and in the presence of a catalyst, such as sodium hydroxide or hydrochloric acid.
The reaction produces a new compound, which is then purified to remove any impurities.

Step 4: Protection of Carboxylate Functionality

The final step in the synthesis of 1,1-dimethylethyl (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.
2.
1]heptane-2-carboxylate involves the protection of the carboxylate functionality.
This is typically achieved by treating the compound with a protecting group, such as t-butyl chloride or benzyl chloride.
This reaction is typically carried out in the presence of a solvent, such as dichlor