1-Piperidinecarboxylicacid,2-methyl-4-oxo-,1,1-dimethylethylester,(2R)-(9CI) Chemical Properties

Melting point:

57.7 °C

Boiling point:

298.8±33.0 °C(Predicted)

Density 

1.060±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-1.52±0.40(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C11H19NO3/c1-8-7-9(13)5-6-12(8)10(14)15-11(2,3)4/h8H,5-7H2,1-4H3/t8-/m1/s1

InChIKey

HQMYWQCBINPHBB-MRVPVSSYSA-N

SMILES

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

1-Piperidinecarboxylicacid,2-methyl-4-oxo-,1,1-dimethylethylester,(2R)-(9CI) Usage And Synthesis

Synthesis

Tert-butyl (R)-2-methyl-4-oxopiperidine-1-carboxylate and 1-N-Boc-2(S)-methyl-piperidin-4-one were synthesized by chiral chromatographic separation using 1-Boc-2-methyl-piperidone as starting material. The procedure was as follows: using a CHIRALPAK ADTM column (size: 4.6×250 mm) with anhydrous ethanol as the mobile phase, the flow rate was set at 1.0 mL/min, and the elution was carried out at the UV detection wavelength of 220 nm. The racemic tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (15.0 g) was separated to finally obtain isomer 1 ((R)-tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate, 5.28 g, 35% yield) and isomer 2 (1-N-Boc-2(S)-methyl-piperidin-4-one, 5.01 g, 33% yield). The 1H NMR (CDCl3) data of the two isomers were in agreement as follows: δ 4.7 (m, 1H), 4.2 (m, 1H), 3.3 (m, 1H), 2.7 (m, 1H), 2.5 (m, 1H), 2.3 (m, 1H), 2.2 (m, 1H), 1.5 (s, 9H), 1.2 (d, 3H).

References

[1] Patent: WO2004/94380, 2004, A1. Location in patent: Page 26-27

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