tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

Name: tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate
Brand: ChemScene
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CAS No. 744183-20-8
Cat. No. CS-W005948
Molecule weight226.32
Purity≥97%
MDL No.MFCD18428076

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tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate|CS-W005948

Structure of 744183-20-8

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General Information

CAS No. 744183-20-8
Cat. No. CS-W005948
Purity ≥97%
MDL No. MFCD18428076
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₂N₂O₂
Molecular Weight 226.32
Synonym(s) N-Boc-exo-3-aminotropane
SMILES N[C@@H]1C[C@@]2([H])CC[C@](C1)([H])N2C(OC(C)(C)C)=O

Description

tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate is a conformationally constrained, sterically protected amino heterocycle featuring a strategically positioned tertiary amine and ester handle. This scaffold delivers high stability under standard conditions, enabling direct incorporation into complex molecular architectures with predictable stereochemistry.

Application

tert-Butyl exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate serves as a conformationally constrained, stereochemically defined building block for medicinal chemistry campaigns. The exo-oriented amino group and tertiary amine functionality enable direct functionalization in standard coupling and reductive amination protocols. Its tert-butyl carbamate protection offers excellent bench stability and compatibility with diverse reaction conditions, facilitating efficient access to complex nitrogen-containing scaffolds relevant to CNS-targeted therapeutics.

Synthesis

Route1
- 207564-70-3
- ~94%
- In-stock
  
  744183-20-8
References
- Stupple, Paul A.; Batchelor, David V.; Corless, Martin; Dorr, Patrick K.; Ellis, David; Fenwick, David R.; Galan, Sebastien R. G.; Jones, Rhys M.; Mason, Helen J.; Middleton, Donald S.; Perros, Manos; Perruccio, Francesca; Platts, Michelle Y.; Pryde, David C.; Rodrigues, Deborah; Smith, Nicholas N.; Stephenson, Peter T.; Webster, Robert; Westby, Mike; Wood, Anthony Journal of Medicinal Chemistry, 2011 , vol. 54, # 1 p. 67 - 77
Route2
- 1006867-18-0
- ~76%
- In-stock
  
  744183-20-8
References
- H. LUNDBECK A/S Patent: WO2009/106534 A1, 2009 ; Location in patent: Page/Page column 74 ; WO 2009/106534 A1
Route3
- 1307867-04-4
- ~%
- In-stock
  
  744183-20-8
References
- DAINIPPON SUMITOMO PHARMA CO., LTD. Patent: US2012/225876 A1, 2012 ; Location in patent: Page/Page column 29 ;

Safety Information

Download SDS

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

Quality Control

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Computational Chemistry Data

TPSA 55.56
LogP 1.8756
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

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 exo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

CAS No. 744183-20-8

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