3-Acetyl-piperidine-1-carboxylic acid tert-butyl ester Chemical Properties

Boiling point:

312.4±35.0 °C(Predicted)

Density 

1.052

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-2.40±0.40(Predicted)

Appearance

Colorless to off-white Solid

InChI

InChI=1S/C12H21NO3/c1-9(14)10-6-5-7-13(8-10)11(15)16-12(2,3)4/h10H,5-8H2,1-4H3

InChIKey

IIDISJMZFQAYKG-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCC(C(C)=O)C1

Safety Information

HS Code 

2933399990

3-Acetyl-piperidine-1-carboxylic acid tert-butyl ester Usage And Synthesis

Synthesis

Methylmagnesium bromide (1.4 M toluene/THF 75/25, 268 mL) was slowly added dropwise to a solution of 1-Boc-N-methoxy-N-methylpiperidine-3-carboxamide (59 g, 0.22 mol) in tetrahydrofuran (THF, 250 mL) at 0 °C and protected by nitrogen, and the temperature of the reaction was controlled not to exceed 15 °C. After dropwise addition, the reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was slowly poured into an ice-water mixture containing 100 mL of ice-acetic acid. The product was extracted with ether (Et2O) and the organic layer was washed with 5% sodium bicarbonate (NaHCO3) solution. The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give tert-butyl 3-acetylpiperidine-1-carboxylate (50 g, quantitative yield).

References

[1] Patent: WO2018/154133, 2018, A1. Location in patent: Page/Page column 48
[2] Patent: US2006/183761, 2006, A1. Location in patent: Page/Page column 27
[3] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 1932 - 1938
[4] Patent: WO2010/36589, 2010, A1. Location in patent: Page/Page column 62
[5] Patent: WO2012/58127, 2012, A2. Location in patent: Page/Page column 80

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