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
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

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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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

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.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  538-09-0
- ~98%
- In-stock
  
  143557-91-9
References
- N.V. ORGANON Patent: WO2007/63071 A1, 2007 ; Location in patent: Page/Page column 15 ; WO 2007/063071 A1
Route2
- 936701-56-3
- ~80%
- In-stock
  
  143557-91-9
References
- Peters, Dan; Munro, Gordon; Nielsen, Elsebet Østergaard Patent: US2012/4257 A1, 2012 ; Location in patent: Page/Page column 7 ; US 20120004257 A1
Route3
- 652148-00-0
- In-stock
  
  34619-03-9
- ~46%
- In-stock
  
  194222-05-4
- In-stock
  
  143557-91-9
References
- WO2004/9588 A1, ; Page 49 ; WO 2004/009588 A1

Safety Information

Download SDS

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

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

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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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