tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-carboxylate
[CAS# 113451-59-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-carboxylate
• Synonyms: (1S,4S)-(-)-2-Boc-2,5-Diazabicyclo[2.2.1]heptane; (1S,4S)-N-(tert-Butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane
• Molecular Formula: C₁₀H₁₈N₂O₂
• Molecular Weight: 198.26
• CAS Registry Number: 113451-59-5
• EC Number: 674-133-3
• SMILES: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Melting point: 74 - 76 °C (Expl.)
• Boiling point: 276.4±15.0 °C 760 mmHg (Calc.)^*
• Flash point: 120.9±20.4 °C (Calc.)^*
• Index of refraction: 1.501 (Calc.)^*
• alpha: -44 ° (c=1 in chloroform)

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H314-H315-H319-H335
• Safety Statements: P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-carboxylate is a chemical compound that belongs to the class of bicyclic amines, specifically a derivative of the diazabicyclo[2.2.1]heptane structure. This compound is characterized by a bicyclic ring system consisting of seven members, with two nitrogen atoms incorporated into the structure. The compound contains a carboxylate group attached to the bicyclic nitrogen-containing ring, as well as a tert-butyl group attached to the carboxylate.

The stereochemistry of this compound, denoted by (1S,4S), specifies the configurations of the two chiral centers present in the bicyclic structure. The specific arrangement of the substituents at these positions plays a crucial role in the compound's chemical and biological properties. This stereochemistry suggests that the compound has a particular three-dimensional shape, which can affect how it interacts with biological systems or participates in chemical reactions.

The synthesis of tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-carboxylate typically involves the formation of the bicyclic ring structure, which can be achieved by a series of synthetic steps. These may include the construction of the bicyclic core using cyclization reactions, followed by the introduction of functional groups such as the carboxylate and tert-butyl groups. One common synthetic strategy involves the use of precursors that undergo ring-closure reactions, often in the presence of activating reagents, to form the bicyclic structure. Once the ring system is formed, selective functionalization reactions are employed to introduce the carboxylate group and the tert-butyl group.

The diazabicyclo[2.2.1]heptane core structure is of particular interest due to its potential for acting as a ligand in coordination chemistry or as a scaffold for drug design. The nitrogen atoms in the bicyclic ring can participate in coordination with metal ions, and this can influence the reactivity and stability of the compound. Moreover, the bicyclic structure can provide a rigid framework that may enhance interactions with biological targets, such as enzymes or receptors, which could make this compound useful in medicinal chemistry.

One of the potential applications of tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-carboxylate is as a building block for the development of bioactive compounds. The diazabicyclic structure has been investigated for its potential to act as a ligand for metal ions in catalytic processes, such as in asymmetric synthesis, or as a ligand in metal-based drug delivery systems. Additionally, the nitrogen atoms in the bicyclic structure may facilitate interactions with proteins or enzymes, making this compound a candidate for further exploration in drug discovery, particularly for diseases involving neurotransmission or enzyme inhibition.

Furthermore, the sterically hindered tert-butyl group could provide stability to the compound, making it more resistant to decomposition or unwanted side reactions. The presence of the carboxylate group could also enable the compound to form salts or interact with other charged species, potentially increasing its solubility in aqueous environments or influencing its pharmacokinetic properties.

In conclusion, tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-carboxylate is a bicyclic compound with a diazabicyclo[2.2.1]heptane core structure. The compound’s stereochemistry and functional groups suggest that it may be valuable in a variety of applications, including drug design, catalytic processes, and coordination chemistry. Further research into its synthesis, reactivity, and interactions with biological systems could reveal additional uses for this compound in medicinal chemistry or material science.