N-Boc-piperazine-2-carboxylic acid methyl ester Chemical Properties

Boiling point:

321.3±37.0 °C(Predicted)

Density 

1.118g/ml

storage temp. 

2-8°C(protect from light)

form 

gel/ oil

pka

7.25±0.40(Predicted)

color 

Yellow

optical activity

-2.9800° (C=0.50 g/100ml, MEOH, 20°C, 589nm)

InChI

InChI=1S/C11H20N2O4/c1-11(2,3)17-10(15)13-6-5-12-7-8(13)9(14)16-4/h8,12H,5-7H2,1-4H3

InChIKey

BRXKHIPPSTYCKO-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCNCC1C(OC)=O

CAS DataBase Reference

129799-15-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43-41-37/38

Safety Statements 

26-36/37/39

HS Code 

2933599590

N-Boc-piperazine-2-carboxylic acid methyl ester Usage And Synthesis

Uses

1-tert-Butyl 2-methyl piperazine-1,2-dicarboxylate is a useful research chemical compound used in the preparation of piperazinylcarbonylaminomethylcarbonylpiperidines as melanocortin-4 receptor agonists.

Synthesis

The general procedure for the synthesis of methyl N-1-Boc-2-piperazinecarboxylate from 4-benzyl 1-tert-butyl 2-methylpiperazine-1,2,4-tricarboxylate is as follows: Example 53 - Preparation of Intermediate 18: The synthesis of Intermediate 18 followed General Procedure 14. To a solution of Intermediate 17 (1-benzyl stirred solution of 4-benzyl 1-methylpiperazine-1,2,4-tricarboxylic acid, 10 g, 26.5 mmol) in MeOH (100 mL) was added 10% Pd/C (30% w/w, 3.0 g). The mixture was placed in a steel vessel and stirred at room temperature under 50 psi hydrogen pressure for 5 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the volatiles were concentrated under reduced pressure to afford 1-tert-butyl 2-methylpiperazine-1,2-dicarboxylate (Intermediate 18, 5.6 g, Yield: 88%) as a light yellow liquid.TLC conditions: 5% methanol-dichloromethane, Rf=0.3.

References

[1] Patent: WO2016/138532, 2016, A1. Location in patent: Paragraph 0288
[2] Patent: US2010/160323, 2010, A1. Location in patent: Page/Page column 47
[3] Patent: US4997836, 1991, A
[4] Patent: EP368670, 1990, A1
[5] Patent: US2004/116518, 2004, A1. Location in patent: Page 42

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