Ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate
[CAS# 365997-33-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate
• Synonyms: (1S,3R,4R)-(+)-3-[(tert-Butoxycarbonyl)amino]-4-hydroxycyclohexanecarboxylic acid ethyl ester
• Molecular Formula: C₁₄H₂₅NO₅
• Molecular Weight: 287.35
• CAS Registry Number: 365997-33-7
• EC Number: 966-581-6
• SMILES: CCOC(=O)[C@H]1CC[C@H]([C@@H](C1)NC(=O)OC(C)(C)C)O

Properties

• Solubility: Slightly soluble (4 g/L) (25 ºC), Calc.^*
• Density: 1.12±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.490, Calc.^*
• Boiling Point: 406.6±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 199.7±28.7 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+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
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate is a chemical compound with significant relevance in the field of synthetic chemistry and drug development. This compound belongs to the class of cyclohexane derivatives and is notable for its complex structure, which includes a hydroxyl group, an amino group protected by a tert-butoxycarbonyl (Boc) group, and an ester group. The stereochemistry of this compound is essential, as it contains specific chiral centers that define its three-dimensional arrangement and, consequently, its reactivity and potential biological activity.

The discovery of ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate stems from ongoing efforts to explore the chemistry of amino alcohol derivatives. These compounds are valuable intermediates in the synthesis of various pharmaceuticals, as they possess functional groups that can be easily modified to introduce a wide range of biological activities. The Boc-protecting group is commonly used to mask the amine functionality during synthetic steps, allowing for selective reactions with other reagents. The hydroxyl group at position 4 is another key feature, as it can participate in further modifications to enhance the compound's pharmacological properties.

The synthesis of ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate typically involves a multi-step process. The cyclohexane ring is often constructed through a combination of stereoselective reactions to ensure the correct configuration at the chiral centers. The introduction of the Boc-protecting group is typically achieved via reaction with Boc2O (di-tert-butyl dicarbonate) under basic conditions, followed by esterification of the carboxylic acid group with ethanol to form the ethyl ester. These synthetic routes require careful control of reaction conditions to avoid racemization or side reactions that could lead to unwanted isomers or byproducts.

One of the key applications of ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate lies in the development of bioactive compounds. The structure of this compound, particularly its amino alcohol core, makes it a useful intermediate in the synthesis of drugs targeting a variety of biological systems. The hydroxyl group can be utilized in the formation of more complex molecules, such as those designed to interact with receptors or enzymes involved in disease processes. The Boc-protected amino group can be deprotected under mild conditions to expose the free amine, which can then be reacted with other functional groups to generate a diverse array of bioactive compounds.

In addition to its potential in drug synthesis, this compound may also find applications in materials science. The ability to modify the structure of cyclohexane derivatives allows for the creation of polymers or other materials with specific properties. For example, incorporating this compound into a polymer matrix could alter the material's mechanical, optical, or thermal properties, making it useful for a variety of industrial applications.

In conclusion, ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate is a valuable chemical compound with applications in drug development and materials science. Its unique structure, including its chiral centers and functional groups, makes it an important intermediate in the synthesis of bioactive molecules. As research continues, this compound may play a role in the development of new therapeutic agents and advanced materials.