(3R,5S)-tert-butyl 3-aMino-5-fluoropiperidine-1-carboxylate丨CAS 1271810-13-9

This compound is primarily used in pharmaceutical and medicinal chemistry as a building block for the synthesis of chiral piperidine-based drugs. The fluorine atom improves metabolic stability, lipophilicity, and target binding in drug candidates, while the protected amino group allows for selective functionalization in multi-step syntheses. It is utilized in the development of central nervous system agents, enzyme inhibitors, and receptor modulators. In organic synthesis, it serves as a key intermediate for constructing heterocyclic scaffolds, peptide mimetics, and other nitrogen-containing bioactive molecules. Its defined stereochemistry is particularly valuable for producing enantiomerically pure compounds, which is essential for achieving optimal pharmacological activity.

The benefits of (3R,5S)-tert-butyl 3-amino-5-fluoropiperidine-1-carboxylate include its high stereochemical purity, chemical versatility, and stability. The tert-butyl carbamate group protects the nitrogen, allowing selective derivatization of the amino group or modification of the fluorinated carbon. The fluorine atom enhances chemical stability, biological activity, and membrane permeability of derivatives. The compound is soluble in common organic solvents and stable under standard laboratory conditions, making it convenient for multi-step synthesis. Its chiral integrity ensures that downstream molecules retain the desired enantiomeric purity, which is crucial for drug development and medicinal chemistry applications.