tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

Name: tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
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CAS No. 143557-91-9
Cat. No. CS-W019359
Purity≥98%
MDL No.MFCD22409620

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tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate|CS-W019359

Structure of 143557-91-9

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Description

tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate features a rigid, bridged bicyclic scaffold with a stereochemically defined hydroxyl group at the 3-endo position and a bench-stable tert-butyl ester handle. This configuration enables direct incorporation into complex alkaloid syntheses and facilitates selective functionalization at the nitrogen-bearing ring junction.

Application

tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate serves as a versatile, bench-stable building block for the synthesis of nitrogen-containing heterocycles. The tertiary alcohol functionality enables direct derivatization via Mitsunobu or oxidation reactions, while the protected carboxylic acid facilitates selective deprotection and coupling. Its rigid bicyclic framework provides defined stereochemistry, supporting its utility in medicinal chemistry campaigns targeting CNS-active compounds and enzyme inhibitors.

General Information

CAS No. 143557-91-9
Cat. No. CS-W019359
Purity ≥98%
MDL No. MFCD22409620
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₁NO₃
Molecular Weight 227.30
Synonym(s) Tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
SMILES O[C@H]1C[C@H]2CC[C@@H](C1)N2C(OC(C)(C)C)=O

Computational Chemistry Data

TPSA 49.77
LogP 1.9092
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
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 Functional Group Alcohol

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

CAS No. 143557-91-9

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