ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives BOC-amino acid Ethyl N-Boc-piperidine-4-carboxylate

Ethyl N-Boc-piperidine-4-carboxylate

Product NameEthyl N-Boc-piperidine-4-carboxylate
CAS142851-03-4
MFC13H23NO4
MW257.33
EINECS000-000-0
MOL File142851-03-4.mol

Chemical Properties

Boiling point	120-135 °C/0.5 mmHg
Density	1.046 g/mL at 25 °C
refractive index	n20/D 1.458
Flash point	>230 °F
storage temp.	Inert atmosphere,2-8°C
solubility	Chloroform, Ethyl Acetate
pka	-2.23±0.40(Predicted)
form	Liquid
color	Clear colorless to pale yellow
InChI	InChI=1S/C13H23NO4/c1-5-17-11(15)10-6-8-14(9-7-10)12(16)18-13(2,3)4/h10H,5-9H2,1-4H3
InChIKey	MYHJCTUTPIKNAT-UHFFFAOYSA-N
SMILES	N1(C(OC(C)(C)C)=O)CCC(C(OCC)=O)CC1
CAS DataBase Reference	142851-03-4(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn
Risk Statements	22-37/38-41
Safety Statements	26-39
WGK Germany	3
HazardClass	IRRITANT
HS Code	29333990
Storage Class	10 - Combustible liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Liquid

Uses

Substrate used in a palladium-catalyzed α-arylation of esters with heterocyclic bromides and chlorides leading to, for example, 4-pyridylpiperidinyl esters.

Uses

Ethyl N-Boc-piperidine-4-carboxylate is used as a reagent to synthesize 3-amino-1-(5-indanyloxy)-2-propanol derivatives as sodium channel blockers to treat stroke patients. Ethyl N-Boc-piperidine-4-carboxylate is also used as a reagent to prepare inhibitors of tumour necrosis factor alpha-converting enzyme.

Synthesis

24424-99-5

142851-03-4

The general procedure for the synthesis of ethyl N-Boc-4-piperidinecarboxylate from di-tert-butyl dicarbonate was as follows: ethyl isopiperidinate (5.00 g, 0.032 mol) and triethylamine (4.9 mL, 0.035 mol) were dissolved in dichloromethane (25 mL) at 0 °C, and the dichloromethane of di-tert-butyl dicarbonate (7.2 g, 0.033 mol) was slowly added ( 25mL) solution. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, it was washed three times with potassium bisulfate solution and then once with brine. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated in vacuum to afford the target product ethyl N-Boc-4-piperidinecarboxylate (8.23 g, 100% yield) as a colorless oil. The structure of the product was confirmed by 1H NMR (C6D6,500MHz) δ 3.88 (q, J=7.5Hz, 2H), 2.52 (m, 1H), 1.60-1.48 (m, 8H), 1.42 (s, 9H), 0.92 (t, 3H) and mass spectra (280.44 (M+Na)+).

References

[1] Patent: US2004/204397, 2004, A1
[2] Patent: US2003/144302, 2003, A1
[3] Patent: US2002/55631, 2002, A1
[4] Patent: US2002/86887, 2002, A1
[5] Patent: US5716965, 1998, A

Ethyl N-Boc-piperidine-4-carboxylate

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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