| Identification | Back Directory | [Name]
3-CYANO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER | [CAS]
914988-10-6 | [Synonyms]
N-BOC-3-cyano-4-oxopiperidine
1-Boc-4-oxopiperidine-3-carbonitrile
TERT-BUTYL 3-CYANO-4-OXOPIPERIDINE-1-CARBOXYLATE
tert-butyl 4-cyano-3-oxopiperidine-1-carboxylate
Tert-butyl 3-cyano-4-oxo-1-piperidinecarboxylate
3-cyano-4-oxo-1-piperidinecarboxylic acid tert-butyl ester
3-CYANO-4-OXO-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
3-Cyano-4-Oxo-1-Piperidinecarboxylic Acid 1,1-Dimethylethyl Ester
1-Piperidinecarboxylic acid,3-cyano-4-oxo-,1,1-dimethylethyl ester | [Molecular Formula]
C11H16N2O3 | [MDL Number]
MFCD11109814 | [MOL File]
914988-10-6.mol | [Molecular Weight]
224.26 |
| Chemical Properties | Back Directory | [Melting point ]
97-99 °C | [Boiling point ]
375.1±42.0 °C(Predicted) | [density ]
1.15±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-3.72±0.40(Predicted) | [color ]
Pale Yellow |
| Hazard Information | Back Directory | [Uses]
3-Cyano-4-oxo-piperidine-1-carboxylic Acid tert-Butyl Ester is a useful research reagent for organic synthesis and other chemical processes. | [Synthesis]
The general procedure for the synthesis of N-Boc-cyano-piperidin-4-one from ethyl 3-((tert-butoxycarbonyl)(2-cyanoethyl)amino)propionate was as follows: ethyl 3-((tert-butoxycarbonyl)(2-cyanoethyl)amino)propionate (17.3 g, 64.0 mmol) was dissolved in 200 mL of toluene and 60% sodium hydride (3.84 g, 96.0 mmol). The reaction mixture was heated to reflux and maintained for 3 hours. Upon completion of the reaction, it was cooled to room temperature, diluted with 200 mL of water, and the pH was subsequently adjusted to 3 with 1 N hydrochloric acid solution.The aqueous phase was extracted with ethyl acetate (200 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether as eluent to afford 7.8 g (51.6% yield) of tert-butyl 3-cyano-4-oxopiperidine-1-carboxylate as a white solid.1H NMR (400 MHz, DMSO-d6) δ 10.87 (s, 1H), 3.89 (s, 2H), 3.46 (t, J=5.8Hz. 2H), 2.28 (t, J=5.8Hz, 2H). | [References]
[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9162 - 9183
[2] Patent: US2015/5277, 2015, A1. Location in patent: Paragraph 0208; 0209
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 17, p. 5195 - 5198
[4] Molecules, 2011, vol. 16, # 3, p. 2626 - 2635
[5] Patent: WO2016/86200, 2016, A1. Location in patent: Page/Page column 139; 140; 519; 520 |
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