tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

CAS No. 156496-89-8
Cat. No. CS-0006476
Molecule weight197.23
Purity≥97%
MDL No.MFCD22394907

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tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate|CS-0006476

Structure of 156496-89-8

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General Information

CAS No. 156496-89-8
Cat. No. CS-0006476
Purity ≥97%
MDL No. MFCD22394907
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₅NO₃
Molecular Weight 197.23
Synonym(s) tert-Butyl 3-oxo-3,6-dihydropyridine-1(2H)-carboxylate
SMILES O=C(N1CC=CC(C1)=O)OC(C)(C)C

Description

tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate is a bench-stable, moisture-tolerant heterocyclic building block featuring a conjugated enone system. This scaffold integrates seamlessly into synthetic routes targeting nitrogen-containing pharmaceutical intermediates, where the electrophilic carbonyl and dihydropyridine ring enable selective functionalization under mild conditions.

Application

tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate serves as a versatile building block for pyridine-based heterocycles, enabling efficient access to substituted dihydropyridines via reductive amination or conjugate addition. The tert-butyl ester group provides excellent bench stability and facilitates straightforward deprotection under mild acidic conditions. Its dual functionality—olefinic C=C bond and carbonyl group—supports diverse transformations, including hydrogenation, nucleophilic addition, and coupling reactions, making it well-suited for medicinal chemistry campaigns targeting bioactive scaffolds.

Synthesis

Route1
- In-stock
  
  224779-27-5
- ~10%
- In-stock
  
  156496-89-8
References
- XI, Ning; WANG, Tingjin; YI, Lei Patent: WO2013/138210 A1, 2013 ; Location in patent: Paragraph 0248 ;
Route2
- 120568-74-3
- ~%
- In-stock
  
  156496-89-8
References
- CERENIS THERAPEUTICS SA; ONICIU, Daniela Carmen; DASSEUX, Jean-Louis Henri; BARBARAS, Ronald; KOCHUBEY, Valery; KOVALSKY, Dmitry; RODIN, Oleg Gennadievich; GEOFFROY, Otto; RZEPIELA, Anna Patent: WO2012/54535 A2, 2012 ;
Route3
- 224779-26-4
- ~%
- In-stock
  
  156496-89-8
References
- Claessens, Sven; Jacobs, Jan; De Kimpe, Norbert Synlett, 2007 , # 5 p. 741 - 744

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 46.61
LogP 1.3624
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

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tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

CAS No. 156496-89-8

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