tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Name: tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 885693-20-9
Cat. No. CS-W005209
Purity≥96%
MDL No.MFCD10697911

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tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate|CS-W005209

Structure of 885693-20-9

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General Information

CAS No. 885693-20-9
Cat. No. CS-W005209
Purity ≥96%
MDL No. MFCD10697911
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₈BNO₄
Molecular Weight 309.21
Synonym(s) tert-Butyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate
SMILES CC(C)(OC(N1CCC=C(B2OC(C)(C(C)(O2)C)C)C1)=O)C

Description

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate integrates a boronate handle with a reducible dihydropyridine scaffold, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling. This bench-stable reagent facilitates the construction of complex nitrogen-containing architectures under mild conditions.

Application

tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate serves as a stable, bench-ready building block for Suzuki-Miyaura coupling reactions. The boronate group enables efficient C–C bond formation under mild conditions, while the dihydropyridine core provides a versatile scaffold for further functionalization. Its tert-butyl ester functionality offers excellent stability and ease of purification, making it ideal for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

Route1
- 180691-65-0
- In-stock
  
  73183-34-3
- ~72%
- In-stock
  
  885693-20-9
References
- Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; Meegalla, Sanath K.; Rudolph, M. Jonathan; Wall, Mark J.; Wilson, Kenneth J.; Desjarlais, Renee L.; Manthey, Carl L.; Molloy, Christopher J. Patent: US2008/51402 A1, 2008 ; Location in patent: Page/Page column 60 ; US 20080051402 A1
Route2
- In-stock
  
  98977-36-7
- ~%
- In-stock
  
  885693-20-9
References
- WO2011/29046 A1, ; WO 2011/029046 A1

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 48
LogP 3.185
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

CAS No. 885693-20-9

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