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| | 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate Basic information |
| Product Name: | 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate | | Synonyms: | 1-tert-butyl 4-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;1-O-tert-butyl 4-O-ethyl 4-cyanopiperidine-1,4-dicarboxylate;1-(1,1-Dimethylethyl) 4-ethyl 4-cyano-1,4-piperidinedicarboxylate;1-Boc-4-cyano-4-piperidinecarboxylic acid ethyl ester | | CAS: | 1016258-66-4 | | MF: | C14H22N2O4 | | MW: | 282.34 | | EINECS: | | | Product Categories: | | | Mol File: | 1016258-66-4.mol |  |
| | 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate Chemical Properties |
| | 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate Usage And Synthesis |
| 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 |
| | 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate Preparation Products And Raw materials |
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