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Chemical Structure| 220389-30-0 Chemical Structure| 220389-30-0

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Chemical Structure| 220389-30-0

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Product Details of [ 220389-30-0 ]

CAS No. :220389-30-0
Formula : C12H19NO5
M.W : 257.28
SMILES Code : O=C(N1CCC(O)=C(C(OC)=O)C1)OC(C)(C)C
MDL No. :MFCD24384124

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Application In Synthesis of [ 220389-30-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 220389-30-0 ]

[ 220389-30-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 24424-99-5 ]
  • [ 71486-53-8 ]
  • [ 220389-30-0 ]
YieldReaction ConditionsOperation in experiment
67% With sodium hydroxide; In tetrahydrofuran; ethyl acetate; EXAMPLE 14A 1-tert-butyl 3-methyl 4-hydroxy-5,6-dihydropyridine-1,3(2H)-dicarboxylate A biphasic solution of <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong> (3.94 g, 20.4 mmol) in THF (50 mL) and 1N NaOH (50 mL) at 0° C. was treated with di-tert-butyl dicarbonate (5.8 g, 26.5 mmol), warmed to room temperature overnight, and partitioned between ethyl acetate and 5M NH4Cl. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 7percent ethyl acetate/hexanes to provide the desired product (3.5 g, 67percent). MS (ESI(+)) m/e 258 (M+H)+; 1H NMR (300 MHz, CDCl3) delta11.97 (s, 1H), 4.05 (s, 2H), 3.78 (s, 3H), 3.57 (t, J=5.8Hz, 2H), 2.37 (t, J=6.1 Hz, 2H), 1.48 (s, 9H).
With triethylamine; In tetrahydrofuran; at 20℃; for 1h; A mixture of methyl 4-oxo-3-piperidine carboxylate hydrochloride (10 g, 0.052 mol), BoC2O(11.3 g, 0.052 mol), and Et3N (7.24 ml, 0.052 mol) in THF (60 mL) is stirred at RT for 1 h. After adding NaHCO3 aq., the reaction mixture is extracted with EtOAc. The combined organic phases are washed with brine and dried (Na2SO4) and concentrated under reduced pressure. The resulting residue is purified by silica gel flash chromatography to give Intermediate 27.7 as a colorless oil; ES-MS: [M+H-tBuf = 202, HPLC: tRet = 3.22, 3.97 min.
 

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