3-PIPERIDINEACETIC ACID, 1-[(1,1-DIMETHYLETHOXY)CARBONYL]-4-OXO-, 1,1-DIMETHYLETHYL ESTER Chemical Properties

Boiling point:

396.6±27.0 °C(Predicted)

Density 

1.086±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-2.05±0.40(Predicted)

Safety Information

HS Code 

2933399990

3-PIPERIDINEACETIC ACID, 1-[(1,1-DIMETHYLETHOXY)CARBONYL]-4-OXO-, 1,1-DIMETHYLETHYL ESTER Usage And Synthesis

Synthesis

To a tetrahydrofuran (THF, 300 mL) solution of diisopropylamine (13.5 mL, 96 mmol) was slowly added n-butyllithium (n-BuLi, 2.5 M in hexane, 32 mL) dropwise at -78 °C. The reaction mixture was slowly warmed to -10 °C and then cooled to -78 °C again. Subsequently, a solution of tert-butyl 4-oxopiperidine-1-carboxylate (10 g, 50 mmol) in THF (50 mL) was added dropwise and stirring was continued for 15 min at -78 °C. Next, a mixed solution of tert-butyl bromoacetate (12.6 mL, 85 mmol) with HMPT (5 mL) in THF (30 mL) was added dropwise, and the reaction mixture was stirred at -78 °C for 4 h before slowly warming up to room temperature. The reaction mixture was quenched with saturated aqueous ammonium chloride (NH4Cl) and extracted with ethyl acetate (EA). After post-treatment and purification by column chromatography (eluent: n-hexane/ethyl acetate=4:1), the target product tert-butyl 3-(2-tert-butoxy-2-oxoethyl)-4-oxopiperidine-1-carboxylate was obtained as 7.6 g (50.6% yield, yellow oil).1H NMR (CDCl3) δ: 4.40-4.20 (m, 2H); 3.25-3.15 (m, 1H). 1H); 3.00-2.80 (m, 2H); 2.70-2.40 (m, 3H); 2.30-2.10 (m, 1H); 1.51 (s, 9H), 1.46 (s, 9H).

References

[1] Patent: WO2008/26172, 2008, A1. Location in patent: Page/Page column 63

3-PIPERIDINEACETIC ACID, 1-[(1,1-DIMETHYLETHOXY)CARBONYL]-4-OXO-, 1,1-DIMETHYLETHYL ESTER(1010814-94-4)Related Product Information

• tert-butyl 3-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate
• 1-(Ethoxycarbonyl)-4-oxo-3-piperidineacetic acid ethyl ester
• 2-(PIPERIDIN-3-YL)-ACETIC ACID ETHYL ESTER
• 1-BOC-3-ETHYL-PIPERIDIN-4-ONE
• 3-PIPERIDINEACETIC ACID, 1-[(1,1-DIMETHYLETHOXY)CARBONYL]-4-OXO-, 1,1-DIMETHYLETHYL ESTER