tert-Butyl [cis-4-hydroxycyclohexyl]carbamate
[CAS# 167081-25-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Carboxylic acid and ester perfume >> Other carboxylic acid esters
• Name: tert-Butyl [cis-4-hydroxycyclohexyl]carbamate
• Synonyms: cis-(4-Hydroxycyclohexyl)carbamic acid tert-butyl ester; cis-4-(tert-Butoxycarbonylamino)cyclohexanol; tert-Butyl N-(cis-4-hydroxycyclohexyl)carbamate
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.29
• CAS Registry Number: 167081-25-6
• EC Number: 835-524-6
• SMILES: CC(C)(C)OC(=O)NC1CCC(CC1)O

Properties

• Solubility: Slightly soluble (7.5 g/L) (25 °C), Calc.^*
• Density: 1.06±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

The development of tert-butyl [cis-4-hydroxycyclohexyl] carbamate stems from advances in carbamate chemistry and the need for stable intermediates in organic synthesis. Carbamates are very useful for protecting alcohols and amines in multistep synthetic processes, allowing selective reactions to occur without interference. Its structure has a six-membered ring in a cis configuration with a hydroxyl group at the 4 position. The tert-butyl carbamate group protects the hydroxyl group, enhancing stability and controlling reactivity during synthesis. It appears as a white crystalline solid that is soluble in organic solvents such as ethanol, dichloromethane, and tetrahydrofuran (THF); it is slightly soluble in water.

tert-butyl [cis-4-hydroxycyclohexyl] carbamate is a key intermediate in the synthesis of various drugs. Its protected hydroxyl group can be selectively deprotected and further functionalized, which helps to generate complex drug molecules. This compound can be used to design prodrugs in which the carbamate group is cleaved in vivo to release the active drug. This strategy can improve the solubility, stability, and bioavailability of the drug. The tert-butyl carbamate group can effectively protect alcohols and amines in multistep syntheses. It can be selectively removed under mild acidic conditions, enabling precise control over the introduction of additional functional groups. The cyclohexane core of tert-butyl [cis-4-hydroxycyclohexyl] carbamate is a versatile scaffold in organic chemistry that can be used to build a variety of chemical structures, including heterocycles and complex natural products.

This compound can be incorporated into polymer chains to introduce functional groups that impart specific properties to the polymer, such as enhanced mechanical strength, chemical resistance, or biocompatibility. It is used to modify the surface of materials, such as nanoparticles or polymers, to introduce hydroxyl groups or other functionalities, which is valuable for creating advanced materials for coatings, adhesives, and sensors.

tert-butyl [cis-4-hydroxycyclohexyl] carbamate is used in analytical chemistry to study reaction mechanisms and the behavior of protecting groups under different conditions. It is a model compound for exploring the stability and reactivity of carbamates. The compound can serve as a ligand or substrate in catalytic processes, including transition metal-catalyzed reactions, providing a reference for the design of efficient and selective catalysts for chemical transformations.

References

2021. Synthesis of BAY 1161116. Synfacts.
DOI: 10.1055/s-0040-1719730

2019. Diastereoselective synthesis of cis-N-Boc-4-aminocyclohexanol with reductive ring opening method using continuous flow. Journal of Flow Chemistry.
DOI: 10.1007/s41981-018-00028-3

2012. Synthesis and structure-activity relationship studies on novel 8-amino-3-[2-(4-fluorophenoxy)ethyl]-1,3-diazaspiro[4.5]decane-2,4-dione derivatives as anticonvulsant agents. Medicinal Chemistry Research.
DOI: 10.1007/s00044-012-0265-x