tert-Butyl rel-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate

CAS No. 273206-92-1
Cat. No. CS-0036945
Purity≥95%
MDL No.MFCD09832898

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tert-Butyl rel-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate|CS-0036945

Structure of 273206-92-1

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Description

tert-Butyl rel-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate features a rigid bicyclic scaffold with defined stereochemistry, enabling precise spatial control in medicinal chemistry applications. The tert-butyl ester group enhances solubility and stability during synthesis, while the primary amine supports direct derivatization. This configuration delivers high fidelity in target engagement for CNS-directed drug discovery projects.

Application

tert-Butyl rel-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate serves as a conformationally constrained, enantiopure building block for medicinal chemistry and natural product synthesis. The bicyclic scaffold imparts rigidity to modulate target binding affinity, while the protected amine and carboxylate functionalities enable sequential functionalization. Bench-stable and compatible with standard peptide coupling and reductive amination protocols, it facilitates efficient access to complex heterocyclic architectures and API intermediates.

General Information

CAS No. 273206-92-1
Cat. No. CS-0036945
Purity ≥95%
MDL No. MFCD09832898
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₈N₂O₂
Molecular Weight None
Synonym(s) (1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hexane-3-carboxylic Acid 1,1-Dimethylethyl Ester
SMILES N[C@H]1[C@@]2([H])[C@]1([H])CN(C2)C(OC(C)(C)C)=O

Computational Chemistry Data

TPSA 55.56
LogP 0.8104
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Fatty ring compounds Cyclopropane compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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tert-Butyl rel-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate

CAS No. 273206-92-1

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