tert-butyl 4-[(1R)-1-aminoethyl]piperidine-1-carboxylate
[CAS# 1036027-86-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: tert-butyl 4-[(1R)-1-aminoethyl]piperidine-1-carboxylate
• Molecular Formula: C₁₂H₂₄N₂O₂
• Molecular Weight: 228.33
• CAS Registry Number: 1036027-86-7
• SMILES: C[C@H](C1CCN(CC1)C(=O)OC(C)(C)C)N

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.485, Calc.^*
• Boiling Point: 310.3±15.0 °C (760 mmHg), Calc.^*
• Flash Point: 141.5±20.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

tert-Butyl 4-[(1R)-1-aminoethyl]piperidine-1-carboxylate is a synthetic organic compound with a core structure comprising a piperidine ring, a tert-butyl carbamate protecting group, and an (R)-1-aminoethyl side chain. This compound, often referred to as a tert-butyl-protected amine derivative, is valued in pharmaceutical and chemical research for its potential role as an intermediate in drug synthesis and its utility in organic transformations. The tert-butyl group offers protection to the amine during reactions, providing researchers with a versatile building block for developing complex molecules.

The synthesis of tert-butyl 4-[(1R)-1-aminoethyl]piperidine-1-carboxylate has roots in classical organic chemistry methods for protecting amine groups, with tert-butyl carbamate (Boc) protection emerging as a widely adopted approach in peptide and pharmaceutical synthesis. Its introduction into various synthetic pathways has allowed for the creation of amine-containing molecules without interference from reactive functional groups. The (R)-stereochemistry of this compound is also significant, as it confers specific chiral properties that can lead to selectivity in biological interactions, which is valuable in designing chiral drugs and other enantioselective applications.

In applications, tert-butyl 4-[(1R)-1-aminoethyl]piperidine-1-carboxylate is primarily used as an intermediate in the production of piperidine-based pharmaceuticals, including compounds with neuroprotective and analgesic properties. The piperidine ring is a core structure in many bioactive molecules, which makes this derivative especially useful for producing new drug candidates. By using the tert-butyl group to temporarily mask the amine, researchers can perform multi-step synthesis reactions without unintentional side reactions, subsequently removing the protecting group under mild acidic conditions when the amine functionality is needed in the target structure.

Beyond drug synthesis, tert-butyl 4-[(1R)-1-aminoethyl]piperidine-1-carboxylate is employed in chemical research involving asymmetric synthesis and chiral catalysis. The compound’s stereochemistry makes it suitable for exploring reactions that favor the formation of one enantiomer over another, a critical factor in producing compounds with specific biological activities. Additionally, the Boc group’s stability under a wide range of reaction conditions makes it suitable for laboratory-scale reactions where selective reactivity is essential.

In summary, tert-butyl 4-[(1R)-1-aminoethyl]piperidine-1-carboxylate is a versatile compound with applications in drug discovery, synthetic organic chemistry, and chiral catalysis. Its structural features make it valuable for developing piperidine-based compounds and enabling selective chemical reactions. As research advances, this compound is likely to remain an important tool in creating and optimizing bioactive molecules.

References

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