(R)-Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate
[CAS# 1357600-61-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: (R)-Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate
• Synonyms: tert-butyl (4R)-4-amino-3,3-dimethylpiperidine-1-carboxylate
• Molecular Formula: C₁₂H₂₄N₂O₂
• Molecular Weight: 228.33
• CAS Registry Number: 1357600-61-3
• SMILES: CC1(CN(CC[C@H]1N)C(=O)OC(C)(C)C)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.470, Calc.^*
• Boiling Point: 293.9±33.0 ºC (760 mmHg), Calc.^*
• Flash Point: 131.6±25.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(R)-Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate is a chiral amine that has garnered attention in organic chemistry and pharmaceuticals due to its unique structural features and versatile applications. The compound belongs to a class of piperidine derivatives, characterized by the presence of a six-membered nitrogen-containing ring that plays a critical role in numerous biological and chemical processes. The tert-butyl group and the amino group in its structure contribute to its reactivity and functionality, making it an attractive candidate for synthetic applications.

The discovery of (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate is closely linked to ongoing research in the development of piperidine-based compounds, which are known for their diverse biological activities. Interest in such compounds has increased due to their relevance in drug discovery, as they can exhibit a range of pharmacological properties including analgesic, anti-inflammatory, and central nervous system effects. As a result, researchers have focused on optimizing synthetic routes to obtain enantiomerically pure versions of these compounds, including (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate.

Synthesis of (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate typically involves asymmetric synthesis techniques that are essential for producing compounds with high enantiomeric purity. Various strategies have been employed, including the use of chiral auxiliary reagents and catalytic asymmetric synthesis. These methods are crucial in the pharmaceutical industry, where the different enantiomers of a compound may exhibit vastly different biological activities, necessitating the production of a specific enantiomer for therapeutic use.

One of the primary applications of (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate is its role as an intermediate in the synthesis of pharmaceutical compounds. Its structure facilitates its incorporation into various drug candidates, particularly those targeting neurological disorders or exhibiting central nervous system activity. The amino and carboxylate functional groups allow for further modifications, enabling the synthesis of complex molecules with desirable pharmacological properties.

Additionally, (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate has potential applications in asymmetric catalysis. The presence of the amino group enables it to act as a chiral ligand in transition metal-catalyzed reactions, which can enhance the selectivity and efficiency of synthetic transformations. This feature further expands its utility in the field of organic synthesis, particularly in the development of new methodologies for producing enantiomerically enriched compounds.

Safety is an important consideration when handling (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate, as with any chemical substance. Researchers and practitioners should adhere to standard laboratory safety protocols, including the use of personal protective equipment and proper waste disposal practices, to mitigate any associated risks.

In summary, (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate is a significant compound in organic synthesis and pharmaceutical chemistry. Its chiral nature and structural features make it an essential building block for the development of various bioactive molecules and catalysts. Ongoing research into its properties and applications continues to highlight its importance in medicinal chemistry and the broader field of organic synthesis.