3-(tert-Butoxycarbonyl)-3-azabicyclo[3.2.1]octane-8-carboxylic acid

Name: 3-(tert-Butoxycarbonyl)-3-azabicyclo[3.2.1]octane-8-carboxylic acid
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CAS No. 1250997-29-5
Cat. No. CS-0051577
Purity≥98%
MDL No.MFCD17016674

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3-(tert-Butoxycarbonyl)-3-azabicyclo[3.2.1]octane-8-carboxylic acid|CS-0051577

Structure of 1250997-29-5

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General Information

CAS No. 1250997-29-5
Cat. No. CS-0051577
Purity ≥98%
MDL No. MFCD17016674
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₁NO₄
Molecular Weight 255.31
Synonym(s) 3-Boc-3-azabicyclo[3.2.1]octane-8-carboxylic acid
SMILES OC([C@H]1[C@H]2CC[C@@H]1CN(C(OC(C)(C)C)=O)C2)=O

Description

This azabicyclic scaffold integrates a tert-butoxycarbonyl-protected amine and a carboxylic acid handle, enabling direct incorporation into peptide macrocycles and constrained peptidomimetics. The rigid bicyclic core enhances conformational preorganization, while the orthogonal functional groups support sequential derivatization under standard coupling conditions.

Application

3-(tert-Butoxycarbonyl)-3-azabicyclo[3.2.1]octane-8-carboxylic acid serves as a versatile scaffold for the synthesis of nitrogen-containing heterocycles, particularly in medicinal chemistry applications. The protected amine and carboxylic acid functionalities enable orthogonal transformations, while the bicyclic core provides conformational rigidity. Its bench-stable tert-butyl ester facilitates straightforward deprotection and derivatization, supporting efficient access to diverse analogs via standard coupling and reduction protocols.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 66.84
LogP 1.9641
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Key Words

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3-(tert-Butoxycarbonyl)-3-azabicyclo[3.2.1]octane-8-carboxylic acid

CAS No. 1250997-29-5

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