4-BENZYLOXYCARBONYLAMINO-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER Chemical Properties

Boiling point:

556.1±50.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.84±0.20(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

288154-16-5(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

29333990

4-BENZYLOXYCARBONYLAMINO-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER Usage And Synthesis

Chemical Properties

White powder

Synthesis

To a solution of compound 2-c (0.50 g, 2.05 mmol) in tetrahydrofuran (THF, 4 mL) was added an aqueous sodium hydroxide solution (0.17 g, 4.30 mmol, 2.10 equiv, 4 mL). The reaction mixture was cooled to 0°C. Benzyl chloroformate (0.32 mL, 2.25 mmol, 1.10 eq.) was slowly added dropwise followed by stirring at room temperature for 24 hours. Upon completion of the reaction, the reaction mixture was washed with ether, then the pH of the aqueous layer was adjusted to 2.5 with 1N hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 4-benzyloxycarbonylaminopiperidine-1,4-dicarboxylic acid mono-tert-butyl ester as a white solid (0.55 g, 71% yield), which was used directly in the next step of the reaction.1H-NMR (CDCl3) δ: 7.29-7.39 (m, 5H), 5.10 (s, 2H), 3.84 (bs, 2H). 3.05-3.15 (m, 2H), 1.95-2.12 (m, 4H), 1.45 (s, 9H).

References

[1] Patent: US2010/168421, 2010, A1. Location in patent: Page/Page column 7
[2] Patent: WO2008/150089, 2008, A1. Location in patent: Page/Page column 15

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