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

CAS No. 914988-10-6
Cat. No. CS-W004426
Molecule weight224.26
Purity≥95%
MDL No.MFCD11109814

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tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate|CS-W004426

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General Information

CAS No. 914988-10-6
Cat. No. CS-W004426
Purity ≥95%
MDL No. MFCD11109814
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₆N₂O₃
Molecular Weight 224.26
Synonym(s) 1-Boc-4-oxopiperidine-3-carbonitrile
SMILES O=C(N1CC(C#N)C(CC1)=O)OC(C)(C)C

Description

tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate features a sterically shielded tert-butyl ester paired with a conjugated cyano-ketone motif, enabling direct incorporation into complex heterocyclic scaffolds. This bench-stable intermediate facilitates efficient access to nitrogen-containing frameworks through reductive amination or nucleophilic addition pathways.

Application

tert-Butyl 3-cyano-4-oxopiperidine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to substituted piperidines via reductive amination or nucleophilic addition. The cyano and oxo groups offer orthogonal reactivity for downstream functionalization, while the tert-butyl carbamate provides excellent bench stability and ease of removal under mild acidic conditions. Its well-defined stereochemistry and compatibility with standard coupling protocols make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

Route1
- 266353-22-4
- ~%
- In-stock
  
  914988-10-6
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 20, # 17 p. 5195 - 5198

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-H312-H315-H319-H332-H335
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P304+P341-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P363-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 70.4
LogP 1.33608
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Functional Group Ketone

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Key Words

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

CAS No. 914988-10-6

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