4-[[(tert-butoxyl)carbonyl]amino]-4-piperidinecarboxylic acid
[CAS# 252720-31-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 4-[[(tert-butoxyl)carbonyl]amino]-4-piperidinecarboxylic acid
• Synonyms: 2-pyridin-4-ylsulfanylacetyl chloride;hydrochloride
• Molecular Formula: C₁₁H₂₀N₂O₄
• Molecular Weight: 244.29
• CAS Registry Number: 252720-31-3
• EC Number: 848-431-0
• SMILES: CC(C)(C)OC(=O)NC1(CCNCC1)C(=O)O

Properties

• Density: 1.2$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 409.8$+/-$45.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 201.7$+/-$28.7 $degree$C (Calc.)^*
• Index of refraction: 1.512 (Calc.)^*

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

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

4-[[(tert-butoxyl)carbonyl]amino]-4-piperidinecarboxylic acid is a functionalized piperidine derivative featuring a carboxylic acid at the 4-position and a Boc-protected amino group on the same carbon. Piperidine derivatives have long been important scaffolds in medicinal chemistry due to their conformational rigidity, basicity, and ability to engage in hydrogen bonding and ionic interactions with biological targets. The introduction of the tert-butoxycarbonyl (Boc) protecting group provides chemical stability to the amino functionality during synthetic transformations, making this compound a versatile intermediate in peptide synthesis and heterocyclic chemistry. Structurally, the compound contains a six-membered saturated nitrogen-containing ring with the carboxylic acid and Boc-protected amino group both attached at the 4-position. The Boc group stabilizes the amino group by forming a carbamate linkage, which is resistant to nucleophilic attack under mild conditions but can be removed under acidic conditions to liberate the free amine. The carboxylic acid group is capable of forming amide bonds, esterification products, or salts, making it reactive in both solution-phase and solid-phase synthesis. The synthesis of 4-[[(tert-butoxyl)carbonyl]amino]-4-piperidinecarboxylic acid generally begins with 4-aminopiperidine-4-carboxylic acid as a precursor. Treatment of the free amine with di-tert-butyl dicarbonate under controlled conditions introduces the Boc group selectively, protecting the amino functionality while leaving the carboxylic acid intact. This strategy allows chemists to conduct further synthetic manipulations at other positions of the molecule or to use the compound as a building block in peptide coupling reactions. This compound is widely used in medicinal chemistry and peptide synthesis. The Boc-protected piperidine can serve as a masked amino acid analog in the preparation of cyclic peptides, peptidomimetics, or small-molecule inhibitors. By protecting the amino group, chemists can selectively activate the carboxyl group for amide bond formation, allowing controlled elongation of peptide chains or the introduction of side-chain modifications. After desired transformations, the Boc group can be removed under acidic conditions to reveal the free amine for subsequent reactions. In addition to peptide synthesis, 4-[[(tert-butoxyl)carbonyl]amino]-4-piperidinecarboxylic acid is useful in the design of heterocyclic and nitrogen-containing small molecules. The piperidine ring imparts conformational rigidity and basicity, which can improve binding interactions with enzymes, receptors, or transporters. The presence of both the carboxylic acid and amino group allows for functionalization to form amides, esters, or salts, which is important in optimizing solubility, pharmacokinetics, and receptor selectivity. The compound is also valuable as a synthetic intermediate for the preparation of substituted piperidines, cyclic amines, and functionalized carbamates. The Boc protecting group facilitates stepwise functionalization, allowing chemists to construct complex molecules while controlling the reactivity of nitrogen atoms. This versatility has made Boc-protected piperidine carboxylic acids widely used in both academic and industrial synthetic chemistry. Overall, 4-[[(tert-butoxyl)carbonyl]amino]-4-piperidinecarboxylic acid exemplifies a protected piperidine derivative that serves as a versatile intermediate in peptide chemistry and heterocyclic synthesis. Its Boc-protected amino group and carboxylic acid functionality allow for selective reactions, making it valuable in the construction of peptides, peptidomimetics, and functionalized small molecules for medicinal chemistry and chemical research.

References

2025. Capivasertib. Pharmaceutical Substances.