1-tert-Butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate
CAS 1263197-89-2
CAS · 1263197-89-2
Product Overview
1-tert-Butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate is a high-purity pharmaceutical-intermediates supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Appearance: | Colorless oil |
|---|---|
| 1H NMR Spectrum: | Conforms |
| Purity: | 95% min |
| Optical Rotation [α] (c=1.1 g/100 mL MeOH): | 10–15° |
Applications
This compound is widely used in medicinal chemistry as a building block for synthesizing chiral piperidine-based drugs, including central nervous system agents, enzyme inhibitors, and receptor modulators. The presence of both ester-protected groups enables selective deprotection and derivatization in multi-step syntheses, facilitating the construction of complex molecules. In peptide and heterocyclic chemistry, it serves as a versatile intermediate for designing conformationally constrained analogues and functionalized scaffolds. It is also employed in structure-activity relationship studies to explore the influence of stereochemistry and piperidine substitutions on biological activity, stability, and pharmacokinetic properties.
Benefits
The benefits of 1-tert-Butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate include its high stereochemical fidelity, multifunctional reactivity, and chemical stability. The Boc-protected nitrogen and methyl ester provide orthogonal protection, allowing selective transformations while preserving the integrity of the free amino group. The defined (3S,5R) stereochemistry ensures predictable enantiomeric outcomes, which is critical for bioactive molecule synthesis. Its solubility in common organic solvents, stability under standard conditions, and compatibility with diverse chemical reactions make it convenient for multi-step synthetic routes and medicinal chemistry applications.
Conclusion
In summary, 1-tert-Butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate is a chiral, multifunctional piperidine intermediate used in medicinal chemistry, peptide synthesis, and organic synthesis. Its stereochemical precision, dual ester protection, and free amino functionality provide versatility for constructing complex bioactive molecules, conformationally constrained analogues, and heterocyclic derivatives. With its stability, reactivity, and stereochemical fidelity, it is a valuable building block for advanced pharmaceutical development and complex chemical synthesis.
Previous
Trans-3-fluorocyclobutane-1-carboxylic Acid丨CAS 123812-79-3
Next
Cis-methyl 2-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate丨CAS 170299-60-2