tert-Butyl 3-bromo-4-oxopiperidine-1-carboxylate

CAS No. 188869-05-8
Cat. No. CS-W001487
Molecule weight278.14
Purity≥95%
MDL No.MFCD06738530

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tert-Butyl 3-bromo-4-oxopiperidine-1-carboxylate|CS-W001487

Structure of 188869-05-8

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General Information

CAS No. 188869-05-8
Cat. No. CS-W001487
Purity ≥95%
MDL No. MFCD06738530
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₆BrNO₃
Molecular Weight 278.14
Synonym(s) N-BOC-3-BROMO-4-OXOPIPERIDINE
SMILES O=C1CCN(CC1Br)C(=O)OC(C)(C)C

Description

tert-Butyl 3-bromo-4-oxopiperidine-1-carboxylate features a brominated piperidine core with a ketone at C4, enabling direct functionalization in medicinal chemistry. The tert-butyl carbamate group provides stability and facilitates deprotection under mild acidic conditions. This versatile intermediate integrates readily into complex heterocyclic scaffolds.

Application

tert-Butyl 3-bromo-4-oxopiperidine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to brominated piperidine scaffolds. The protected amine and ketone functionalities offer orthogonal reactivity, facilitating downstream functionalization via nucleophilic substitution or reduction. Its bench-stable nature and compatibility with standard coupling protocols make it ideal for modular synthesis of bioactive compounds.

Synthesis

Route1
- 79099-07-3
- ~82%
- In-stock
  
  188869-05-8
References
- Provins, Laurent; Denonne, Frederic; Celanire, Sylvain; Christophe, Bernard; Defays, Sabine; Delaunoy, Christel; Delporte, Marie-Laure; Demaude, Thierry; Durieu, Veronique; Gillard, Michel; Hubert, Delphine; Lamberty, Yves; Lorent, Genevieve; Valade, Anne; Vanbellinghen, Alain; Vanhoutvin, Nathalie ChemMedChem, 2012 , vol. 7, # 12 p. 2087 - 2092
Route2
- 211108-48-4
- ~72%
- In-stock
  
  188869-05-8
References
- Suennemann, Hans Wolf; Hofmeister, Anja; Magull, Joerg; De Meijere, Armin Chemistry - A European Journal, 2006 , vol. 12, # 32 p. 8336 - 8344
Route3
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  188869-05-8
References
- Journal of Medicinal Chemistry, , vol. 41, # 9 p. 1409 - 1416

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

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Computational Chemistry Data

TPSA 46.61
LogP 1.9598
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Ketone

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

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tert-Butyl 3-bromo-4-oxopiperidine-1-carboxylate

CAS No. 188869-05-8

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