3-exo-Hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Name: 3-exo-Hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 194222-05-4
Cat. No. CS-0048100
Purity≥97%
MDL No.MFCD16294321

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3-exo-Hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester|CS-0048100

Structure of 194222-05-4

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General Information

CAS No. 194222-05-4
Cat. No. CS-0048100
Purity ≥97%
MDL No. MFCD16294321
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₁NO₃
Molecular Weight 227.30
Synonym(s) tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
SMILES O=C(N1[C@H]2C[C@@H](O)C[C@@H]1CC2)OC(C)(C)C

Description

tert-Butyl (1R,3s,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate features a rigid bicyclic scaffold with defined stereochemistry, enabling precise spatial control in medicinal chemistry applications. The hydroxyl group at C3 offers a site for derivatization, while the tert-butyl ester ensures stability and ease of handling under standard conditions.

Application

tert-Butyl (1R,3s,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate serves as a stereochemically defined building block for the synthesis of biologically active nitrogen-containing heterocycles. The tertiary alcohol functionality enables direct functionalization or protection, while the bicyclic scaffold provides conformational rigidity advantageous in medicinal chemistry. Its tert-butyl ester group offers excellent bench stability and facilitates purification via standard chromatographic methods. This compound functions effectively in coupling reactions and serves as a key intermediate in the construction of complex alkaloid-like scaffolds.

Synthesis

Route1
- 937734-25-3
- ~97%
- In-stock
  
  194222-05-4
References
- Nettekoven, Matthias; Plancher, Jean-Marc; Richter, Hans; Roche, Olivier; Taylor, Sven Patent: US2007/123525 A1, 2007 ; Location in patent: Page/Page column 20 ; US 20070123525 A1
Route2
- 652148-00-0
- In-stock
  
  34619-03-9
- ~37%
- In-stock
  
  194222-05-4
- In-stock
  
  143557-91-9
References
- PFIZER PRODUCTS INC. Patent: WO2004/9588 A1, 2004 ; Location in patent: Page 49 ; WO 2004/009588 A1
Route3
- In-stock
  
  185099-67-6
- ~24%
- In-stock
  
  194222-05-4
- In-stock
  
  143557-91-9
References
- GRUeNENTHAL GMBH; MERLA, Beatrix; OBERBOeRSCH, Stefan; REICH, Melanie; SCHUNK, Stefan; JOSTOCK, Ruth; HEES, Sabine; ENGELS, Michael; GERMANN, Tieno; BIJSTERVELD, Edward Patent: WO2010/99938 A1, 2010 ; Location in patent: Page/Page column 106 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 49.77
LogP 1.9092
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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

Key Words

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3-exo-Hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

CAS No. 194222-05-4

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