| Identification | Back Directory | [Name]
3-Acetyl-piperidine-1-carboxylic acid tert-butyl ester | [CAS]
858643-92-2 | [Synonyms]
1-Boc-3-acetylpiperidine
tert-butyl 3-acetylpiperidine-1-carboxylate
1,1-Dimethylethyl 3-acetyl-1-piperidinecarboxylate
3-Acetyl-1-piperidinecarboxylic acid tert-butyl ester
3-Acetyl-piperidine-1-carboxylic acid tert-butyl ester
1-Piperidinecarboxylic acid, 3-acetyl-, 1,1-dimethylethyl es...
1-Piperidinecarboxylic acid, 3-acetyl-, 1,1-diMethylethyl ester | [EINECS(EC#)]
200-589-5 | [Molecular Formula]
C12H21NO3 | [MDL Number]
MFCD09953372 | [MOL File]
858643-92-2.mol | [Molecular Weight]
227.3 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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