| Identification | Back Directory | [Name]
1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate | [CAS]
1016258-66-4 | [Synonyms]
1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate
1-O-tert-butyl 4-O-ethyl 4-cyanopiperidine-1,4-dicarboxylate
1-(tert-Butoxycarbonyl)-4-cyanopiperidine-4-carboxylic acid ethyl ester
4-CYANO-PIPERIDINE-1,4-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 4-ETHYL ESTER
1,4-Piperidinedicarboxylic acid, 4-cyano-, 1-(1,1-dimethylethyl) 4-ethyl ester | [Molecular Formula]
C14H22N2O4 | [MDL Number]
MFCD15144556 | [MOL File]
1016258-66-4.mol | [Molecular Weight]
282.34 |
| Hazard Information | Back Directory | [Synthesis]
At -78 °C, lithium hexamethyldisilazamate (1 M, 20 mL, 20 mmol) was slowly added dropwise to a solution of N-Boc-4-cyanopiperidine (2.1 g, 10 mmol) in anhydrous tetrahydrofuran (30 mL). The reaction mixture was stirred continuously at this temperature for 1 hour. Subsequently, ethyl chloroformate (2.2 g, 20 mmol) was added at -78 °C and stirring was continued at the same temperature for 1 hour. Upon completion of the reaction, the reaction was quenched with 1 M aqueous sodium bicarbonate (30 mL) and extracted with ethyl acetate (100 mL x 3). The organic layers were combined, washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography using a petroleum ether solution of 10-25% ethyl acetate as eluent to afford 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate as a colorless oil (2.8 g, 99% yield).LCMS (ESI) m/z 183.1 [M-99]+. | [References]
[1] Patent: WO2015/78374, 2015, A1. Location in patent: Page/Page column 708
[2] Patent: US2016/340309, 2016, A1. Location in patent: Paragraph 0281; 0282; 0283
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 119 - 124
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5910 - 5915
[5] Patent: WO2008/75110, 2008, A1. Location in patent: Page/Page column 126-127 |
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