(1R,3S,4S)-2-{[(2-Methyl-2-propanyl)oxy]carbonyl}-2-azabicyclo[2.2.1]heptane-3-carboxylic acid(CAS: 291775-59-2)

(1R,3S,4S)-2-{[(2-Methyl-2-propanyl)oxy]carbonyl}-2-azabicyclo[2.2.1]heptane-3-carboxylic acid is a colorless solid with a molecular weight of approximately 287.38 g/mol. It has a pKa of around 2.5 and is poorly soluble in water but soluble in organic solvents. It is slightly basic in nature and exhibits moderate reactivity with nucleophiles. This compound is often used in medicinal chemistry due to its structural complexity and potential biological activity.

(1R,3S,4S)-2-{[(2-Methyl-2-propanyl)oxy]carbonyl}-2-azabicyclo[2.2.1]heptane-3-carboxylic acid is synthesized through multistep reactions involving protected azabicyclic structures, followed by deprotection and functional group manipulation. Common methods include using protecting groups such as tert-butyldimethylsilyl (TBS) groups and employing Lewis acids like trifluoromethanesulfonic anhydride (TFMSA) for the introduction of the carbonyl functionality. The overall yield is typically around 70-80%. This synthesis requires careful control of conditions to achieve the desired stereochemistry.

(1R,3S,4S)-2-{[(2-Methyl-2-propanyl)oxy]carbonyl}-2-azabicyclo[2.2.1]heptane-3-carboxylic acid finds applications in the pharmaceutical industry due to its potential as a drug candidate. It is also used in the development of sensors and in polymer chemistry for its unique structure. This compound's biological activity makes it a valuable tool in medicinal chemistry and materials science research.

When handling (1R,3S,4S)-2-{[(2-Methyl-2-propanyl)oxy]carbonyl}-2-azabicyclo[2.2.1]heptane-3-carboxylic acid, it is essential to wear personal protective equipment (PPE) including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or fume hood to minimize inhalation risks. Spills should be carefully neutralized and cleaned up according to standard procedures. Always refer to the Material Safety Data Sheet (MSDS) or Safety Data Sheet (SDS) for detailed handling and disposal instructions. This compound is not highly toxic but exhibits mild skin and eye irritation, so caution is advised.