tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate is a Boc-protected piperidine derivative offering a constrained cyclic scaffold. The compound aids studies of backbone rigidity, steric influence, and conformational restriction. Researchers employ it to construct peptidomimetic backbones and ligand frameworks. Its protected amine enhances synthetic control.
CAT No: R2173
CAS No:952182-04-6
Synonyms/Alias:tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate;952182-04-6;tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate;4-Amino-1-Boc-2-methylpiperidine;TERT-BUTYL 4-AMINO-2-METHYL-1-PIPERIDINECARBOXYLATE;MFCD09832897;DTXSID40718859;tert-butyl (2S,4S)-4-amino-2-methylpiperidine-1-carboxylate;1434073-24-1;tert-butyl trans-4-amino-2-methylpiperidine-1-carboxylate;tert-Butyl cis-4-amino-2-methylpiperidine-1-carboxylate;MFCD22397554;MFCD22397558;MFCD26954786;MFCD26954787;(2R,4R)-1-Boc-4-amino-2-methylpiperidine;(2R,4S)-1-Boc-4-amino-2-methylpiperidine;SCHEMBL1064684;(2R,4R)-4-Amino-2-methyl-piperidine-1-carboxylic acid tert-butyl ester;DTXCID90669605;OGIPSHDJYIEDKG-UHFFFAOYSA-N;4-AMINO-2-METHYL-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;AKOS015855180;PB20392;SB13025;SB13026;SB13027;SB13028;SB23157;SB23158;AS-33389;SY042076;SY270103;SY270462;SY278115;SY292887;DB-349045;CS-0048232;(2S,4R)-4-Amino-1-Boc-2-methylpiperidine;(2S,4S)-4-Amino-1-Boc-2-methylpiperidine;EN300-184233;tert-Butyl4-amino-2-methylpiperidine-1-carboxylate;1-(tert-butoxycarbonyl)-4-amino-2-methylpiperidine;cis-4-Amino-2-methyl-piperidine-1-carboxylic acid tert-butyl ester;(2R,4S)-4-Amino-2-methyl-piperidine-1-carboxylic acid tert-butyl ester;trans-4-Amino-2-methyl-piperidine-1-carboxylic acid tert-butyl ester;824-320-2;
tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate is a versatile carbamate-protected piperidine derivative that plays a significant role in modern synthetic organic chemistry. Characterized by its robust tert-butoxycarbonyl (Boc) protection on the amine group and a methyl substitution at the 2-position, this compound offers enhanced stability and selective reactivity under a broad range of reaction conditions. Its structural features make it highly valuable for researchers seeking efficient intermediates in the assembly of complex molecular architectures. The presence of both a protected amine and a substituted piperidine ring allows for diverse functionalization strategies, enabling precise control over subsequent chemical transformations. As a result, tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate is frequently employed in the development of advanced materials, fine chemicals, and various classes of bioactive molecules.
Pharmaceutical intermediate synthesis: In the realm of pharmaceutical research and development, tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate serves as a key intermediate for constructing a variety of heterocyclic scaffolds. Its Boc-protected amine functionality allows for selective deprotection, enabling the introduction of the piperidine core into more complex molecular frameworks. The compound's unique substitution pattern facilitates the synthesis of analogs that can be further functionalized, supporting the rapid exploration of structure-activity relationships. By incorporating this intermediate into multi-step synthetic routes, chemists can efficiently access libraries of candidate molecules for medicinal chemistry programs, expediting the lead optimization process.
Peptide and peptidomimetic design: The protected amine group of tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate makes it particularly valuable in the synthesis of peptidomimetics and modified peptides. The compound's piperidine ring can mimic the structural and conformational attributes of proline or other cyclic amino acids, thereby modulating the physicochemical properties and biological activities of peptide-based molecules. Researchers utilize this building block to introduce conformational constraints, enhance metabolic stability, and improve receptor selectivity in peptide analogs. Its compatibility with standard peptide coupling protocols and orthogonal protection strategies further streamlines the assembly of sophisticated peptide structures.
Agrochemical research: In agrochemical discovery, 4-amino-2-methylpiperidine derivatives, including tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate, are frequently explored as synthetic intermediates for developing new crop protection agents. The compound's functional group versatility enables the rapid generation of diverse analogs, facilitating structure-activity studies aimed at optimizing efficacy and selectivity. Its incorporation into agrochemical candidates can improve physicochemical properties such as solubility and stability, thereby enhancing performance in field applications. As a result, it plays a pivotal role in the iterative design and synthesis of next-generation agricultural chemicals.
Material science innovation: The unique structural attributes of tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate also position it as a valuable intermediate in the development of advanced materials. Researchers leverage its piperidine core and protected amine group to introduce functional moieties into polymers, dendrimers, and other macromolecular systems. The compound's compatibility with a range of polymerization and post-functionalization techniques allows for the precise tuning of material properties, such as mechanical strength, thermal stability, or chemical reactivity. Its use in material science extends to the design of specialty coatings, responsive surfaces, and molecular recognition elements.
Organic synthesis methodology: The chemical versatility of tert-Butyl 4-amino-2-methylpiperidine-1-carboxylate underpins its widespread adoption in the development of novel synthetic methodologies. Chemists employ it as a model substrate for exploring new catalytic transformations, protecting group strategies, and regioselective functionalizations. Its well-defined reactivity profile facilitates the optimization of reaction conditions and the evaluation of new synthetic concepts. By serving as a reliable and adaptable building block, this compound contributes to the advancement of synthetic organic chemistry, supporting the discovery of innovative routes to complex molecules across multiple research domains.
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