(2R,5S)-2,5-DIMETHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

280℃

Density 

0.970

Flash point:

123℃

storage temp. 

2-8°C(protect from light)

pka

8.55±0.60(Predicted)

form 

solid

color 

Colourless to light yellow / liquid

InChI

InChI=1S/C11H22N2O2/c1-8-7-13(9(2)6-12-8)10(14)15-11(3,4)5/h8-9,12H,6-7H2,1-5H3/t8-,9+/m0/s1

InChIKey

PGZCVLUQTJRRAA-DTWKUNHWSA-N

SMILES

N1(C(OC(C)(C)C)=O)C[C@H](C)NC[C@H]1C

Safety Information

HS Code 

2933599590

(2R,5S)-2,5-DIMETHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

Tert-butyl 4-(4-fluorobenzyl)-(2R,5S)-dimethylpiperazine-1-carboxylate (37.8 g, 117.4 mmol) was used as a raw material and dissolved in a mixture of methanol (250 mL) and glacial acetic acid (30 mL). The mixture was transferred to a 2 L hydrogenation flask, purged with nitrogen and stirred for 10 min. Subsequently, palladium hydroxide (3.8 g, 20 wt%) was added to the mixture and the reaction was shaken at room temperature and 40 psi hydrogen pressure for 48 hours. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and washed with methanol. The filtrate was concentrated to dryness on a rotary evaporator to afford 37.64 g (100% yield) of the target product (2R,5S)-tert-butyl (2R,5-Dimethylpiperazine-1-carboxylate), which was detected by mass spectrometry showing the M+H+ peak at 215.

References

[1] Patent: US2004/142940, 2004, A1. Location in patent: Page/Page column 29
[2] Patent: US2004/142940, 2004, A1. Location in patent: Page/Page column 44-45
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 828 - 831

(2R,5S)-2,5-DIMETHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(309915-46-6)Related Product Information

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