4-(2-ETHOXYCARBONYL-ACETYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

386.1±32.0 °C(Predicted)

Density 

1.113±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

10.39±0.20(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

479630-08-5

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

29333990

4-(2-ETHOXYCARBONYL-ACETYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

N-BOC-4-(2-ethoxycarbonylacetyl)piperidine is a piperidine derivative and an important organic synthesis intermediate with broad application prospects in medicine, scientific research and other fields.

Synthesis

General procedure for the synthesis of tert-butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate from ethanol and compound (CAS:1336874-02-2): tert-butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate (3) was added to anhydrous ethanol (200 mL) and the solution was refluxed for 48 hours. Upon completion of the reaction, the solution was concentrated under vacuum and purified by fast chromatography (eluent: dichloromethane) to afford the product 3 as a slightly reddish oil (14.36 g, 85% yield). The product characterization data were as follows: 1H NMR (500 MHz, CDCl3) δ 12.09 (s, 0.14H, allyl OH), 4.89 (s, 0.14H, allyl CH), 4.13 (q, J = 7Hz, 2H), 4.10-3.96 (m, 2H), 3.42 (s, 2H), 2.81-2.67 (m, 2H), 2.62-2.52 (m, 2H). 2.62-2.52 (m, 1H), 1.85-1.71 (m, 2H), 1.55-1.43 (m, 2H), 1.39 (s, 9H), 1.21 (t, J = 7Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 204.0, 180.2 (alkenols), 172.7 (enol), 167.0, 154.4, 87.52, 79.51, 61.3, 48.5, 47.1, 28.2, 27.1, 13.9; thin-layer chromatography Rf = 0.2 (dichloromethane). High-resolution mass spectrometry (HRMS) calculated value C15H26NO5(M + H)+ 300.1805, measured value 300.1808.

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7193 - 7205
[2] Patent: WO2013/25939, 2013, A2. Location in patent: Page/Page column 69; 71

4-(2-ETHOXYCARBONYL-ACETYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(479630-08-5)Related Product Information

• 3-(2-ETHOXYCARBONYL-ACETYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE
• METHYL N-BOC-4-PIPERIDINEPROPIONATE
• 4-(2-ETHOXYCARBONYL-ACETYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• ETHYL-4-PIPERIDINOYL-ACETATE
• N-Boc-4-piperidinepropionic acid
• 4-Acetyl-piperidine-1-carboxylic acid tert-butyl ester