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3-Methylene-piperidine-1-carboxylic acid tert-butyl ester
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CAS No. 276872-89-0
- Cat. No. CS-D0759
- Purity≥97%
- MDL No.MFCD08706141
*For research and further manufacturing use only, not for direct human use.
Structure of 276872-89-0
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General Information
- CAS No. 276872-89-0
- Cat. No. CS-D0759
- Purity ≥97%
- MDL No. MFCD08706141
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₁₉NO₂
- Molecular Weight 197.27
- Synonym(s) tert-butyl 3-methylidenepiperidine-1-carboxylate
- SMILES O=C(OC(C)(C)C)N(CCC1)CC1=C
Description
3-Methylene-piperidine-1-carboxylic acid tert-butyl ester features a reactive exocyclic methylene group conjugated to a piperidine ring, enabling direct functionalization in synthetic transformations. The tert-butyl ester moiety provides stability and facilitates selective deprotection under mild acidic conditions. This scaffold integrates readily into complex heterocyclic architectures and serves as a key intermediate in medicinal chemistry campaigns targeting CNS-active compounds and kinase inhibitors.
Application
3-Methylene-piperidine-1-carboxylic acid tert-butyl ester serves as a versatile building block for the synthesis of nitrogen-containing heterocycles and bioactive molecules. Its conjugated enamine functionality enables efficient Michael additions, cycloadditions, and transition-metal-catalyzed couplings. The tert-butyl ester group provides excellent bench stability and facilitates straightforward deprotection under mild acidic conditions, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.
Synthesis
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References
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US2009/275585 A1, ; Page/Page column 13; 17 ; US 20090275585 A1
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Route2
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In-stock
98977-36-7 - ~%
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In-stock
276872-89-0
References
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WO2006/85212 A2, ; Page/Page column 44 ;
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Route3
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In-stock
24424-99-5 -
357289-94-2 - ~57%
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In-stock
276872-89-0
References
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Prevost, Natacha; Shipman, Michael Organic Letters, 2001 , vol. 3, # 15 p. 2383 - 2385
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 29.54
- LogP 2.5735
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 0
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Key Words
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