(S)-Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate
[CAS# 1357600-60-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: (S)-Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate
• Synonyms: tert-butyl (4S)-4-amino-3,3-dimethylpiperidine-1-carboxylate
• Molecular Formula: C₁₂H₂₄N₂O₂
• Molecular Weight: 228.33
• CAS Registry Number: 1357600-60-2
• 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 °C (760 mmHg), Calc.^*
• Flash Point: 131.6±25.4 °C, Calc.^*

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

Safety Data

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

Discovery and Applications

(S)-Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate is a chiral building block that has gained prominence in the field of organic chemistry and pharmaceuticals. Its unique structure features a piperidine ring, which is a six-membered nitrogen-containing heterocycle known for its versatility in synthetic applications. The presence of the tert-butyl group and the amino functional group contribute to the compound's reactivity and its potential utility in various chemical reactions.

The discovery of (S)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate can be linked to ongoing research focused on piperidine derivatives and their applications in drug development. The interest in piperidine compounds has grown due to their wide-ranging biological activities, including analgesic, anti-inflammatory, and central nervous system effects. Researchers have been exploring ways to synthesize and modify these compounds to enhance their pharmacological properties and selectivity.

The synthesis of (S)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate typically involves asymmetric synthesis methods that produce the desired enantiomer. Various approaches have been developed to achieve high enantiomeric purity, including chiral auxiliary strategies and enzymatic resolutions. The ability to produce enantiomerically pure compounds is crucial in the pharmaceutical industry, as the biological activity of enantiomers can vary significantly.

One of the primary applications of (S)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate is in the synthesis of pharmaceutical intermediates. Its structure makes it an attractive building block for the development of various bioactive molecules. For example, it can be utilized in the synthesis of drugs targeting neurological disorders or as an intermediate in the preparation of other piperidine derivatives with enhanced therapeutic profiles.

Moreover, (S)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate has been investigated for its potential role in the design of new catalysts and ligands in asymmetric synthesis. The presence of the amino and carboxylate functional groups allows for the formation of various coordination complexes, which can facilitate enantioselective reactions. This aspect of the compound enhances its value in synthetic organic chemistry and expands its applicability in the field of catalysis.

Safety considerations are essential when handling and working with (S)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate, as with any chemical compound. Proper laboratory practices, including the use of personal protective equipment and adherence to safety protocols, should be observed to mitigate any risks associated with its use.

In conclusion, (S)-tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate is a significant compound in the realm of organic synthesis and pharmaceutical development. Its unique structure and versatile applications make it an important building block for the creation of bioactive molecules and catalysts. Continued research into its properties and potential applications is likely to yield valuable contributions to medicinal chemistry and organic synthesis.

References

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