((1S,4S)-4-Hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester
[CAS# 1351997-30-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: ((1S,4S)-4-Hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester
• Synonyms: tert-butyl N-[(1S,4S)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl]carbamate
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.33
• CAS Registry Number: 1351997-30-2
• SMILES: CC(C)(C)OC(=O)N[C@H]1CC[C@@H](C2=CC=CC=C12)O

Discovory and Applicatios

((1S,4S)-4-Hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester is a chiral carbamate derivative in which a tetrahydronaphthalene core is functionalized with a hydroxyl group at the 4-position and a carbamate moiety at the 1-position, protected with a tert-butyl group. The stereochemistry at the 1- and 4-positions is of the S-configuration, which is crucial for its chemical reactivity and potential interactions in biological systems. The combination of a secondary alcohol and a protected carbamate provides multiple reactive sites, making this compound a versatile intermediate in the synthesis of pharmaceuticals and complex heterocyclic molecules.

The synthesis of this carbamate derivative generally involves the selective protection of the amino or hydroxyl functionality of the corresponding chiral tetrahydronaphthalene derivative. Formation of the carbamate is achieved by reacting the primary amine with a tert-butyl chloroformate or equivalent carbamoylating reagent under controlled conditions to ensure selectivity and preservation of stereochemistry. The hydroxyl group remains unprotected, allowing potential further functionalization. Purification is commonly achieved by recrystallization or column chromatography, yielding a solid product with defined chemical and physical properties.

In synthetic chemistry, the compound serves as a valuable intermediate for the construction of substituted tetrahydronaphthalene derivatives and other chiral molecules. The carbamate group can be selectively deprotected under acidic conditions to reveal the free amine, enabling acylation, sulfonylation, or heterocyclic ring formation. The hydroxyl group at the 4-position allows etherification, esterification, or oxidation reactions, providing additional pathways for derivatization. These functional handles make the compound suitable for assembling complex molecular scaffolds with tunable chemical and biological properties.

In medicinal chemistry, derivatives derived from this compound have potential applications as chiral ligands, enzyme inhibitors, or bioactive scaffolds. The bicyclic core imparts rigidity and planarity, while the hydroxyl and carbamate functionalities allow hydrogen bonding and other non-covalent interactions with biological targets. By modifying the substituents or deprotecting the carbamate, the molecule can be adapted to interact with specific proteins or receptors, supporting structure–activity relationship studies and optimization of pharmacological properties.

The compound also finds utility in methodology development and chemical research. Its dual functionality and defined stereochemistry make it suitable for studying stereoselective reactions, protective group strategies, and cross-coupling methodologies. Researchers use such derivatives to explore the reactivity of carbamates and secondary alcohols in chiral environments, investigating regioselectivity, reaction kinetics, and catalytic performance.

Physically, ((1S,4S)-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester is generally obtained as a crystalline solid with moderate solubility in polar organic solvents such as dimethylformamide, dichloromethane, and ethanol. It is stable under standard laboratory conditions but should be protected from strong acids, bases, and oxidizing agents that could compromise the carbamate or hydroxyl group. Proper storage ensures chemical integrity and suitability for multistep synthesis or biological evaluation.

Overall, ((1S,4S)-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester is a versatile chiral intermediate combining a hydroxyl group and a protected carbamate on a tetrahydronaphthalene scaffold. Its stereochemistry and functional groups allow selective chemical transformations and derivatization, making it a valuable building block for the synthesis of bioactive compounds, chiral ligands, and complex heterocyclic structures in medicinal and synthetic organic chemistry.

References

2024. Method for preparing tetrahydro-1-naphthylamine and derivatives thereof. WO Patent, 2024153159.

2021. Crystal form of an opioid receptor (MOR) agonist and preparation method. CN Patent, 112638906.