617714-22-4 | 2-Azabicyclo[2.2.2]octane-2-carboxylic acid, 5-oxo-1,1-dimethylethyl ester

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$82.00	$57.00
250mg	98%	in stock	$148.00	$103.00
1g	98%	in stock	$315.00	$221.00
5g	98%	in stock	$962.00	$674.00

Description

• Catalog Number: AG80069
• Chemical Name: 2-Azabicyclo[2.2.2]octane-2-carboxylic acid, 5-oxo-1,1-dimethylethyl ester
• CAS Number: 617714-22-4
• Molecular Formula: C12H19NO3
• Molecular Weight: 225.2842
• MDL Number: MFCD17016701
• SMILES: O=C1CC2CCC1CN2C(=O)OC(C)(C)C

Upstream Synthesis Route

The synthesis route for 2-Azabicyclo[2.2.2]octane-2-carboxylic acid, 5-oxo-1,1-dimethylethyl ester can be outlined as follows:

1. Begin with the cycloaddition reaction between a suitable diene and a dienophile to form the bicyclic structure. In this case, cycloaddition of cyclopentadiene with maleic anhydride can be used to form the norbornene system.

2. Perform a hydrogenation reaction to reduce the double bonds and obtain the saturated bicyclic system: 2-azabicyclo[2.2.2]octane.

3. Introduce the carboxylic acid functionality through oxidizing the corresponding alcohol. This can be achieved through an oxidation reaction using an oxidizing agent like potassium permanganate (KMnO4) or chromium(VI) oxide (CrO3) in an acidic medium.

4. Activate the carboxylic acid group for esterification by converting it to an acid chloride using thionyl chloride (SOCl2) or oxalyl chloride (COCl)2.

5. The acid chloride can then be reacted with 2-methylpropan-2-ol under Lewis acid catalysis to form the desired ester: 2-Azabicyclo[2.2.2]octane-2-carboxylic acid, 5-oxo-1,1-dimethylethyl ester. A catalytic amount of pyridine or triethylamine can be used to neutralize the formed HCl.

6. Perform a subsequent oxidation step if necessary to introduce the 5-oxo- functionality on the bicyclic structure, utilizing an appropriate oxidant like Dess-Martin periodinane or PCC (Pyridinium chlorochromate).

7. Carry out purification steps, such as recrystallization or column chromatography, to isolate and purify the final product.

Throughout the process, it is critical to monitor reaction progress and purity of intermediates using techniques such as TLC (Thin Layer Chromatography), GC (Gas Chromatography), or HPLC (High-Performance Liquid Chromatography). Adjustments in reaction conditions may be necessary to optimize yields and selectivity for each step.