Ethyl Acetate → HCID 10923105, compound

HRID 1374404Notes

Reaction equation

HRID 1374404 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:10][C:11]([N:13]([CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C@H:14]([C:16]([O:18]C)=O)[CH3:15])=[O:12])[CH:8]=[CH2:9].P([O-])(O)(O)=O.[Na+].C(OCC)(=O)C>C1COCC1>[CH3:15][C@H:14]1[C:16](=[O:18])[CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20][N:13]1[C:11]([O:10][CH2:7][CH:8]=[CH2:9])=[O:12].[CH3:15][C@H:14]1[C:16](=[O:18])[CH:22]([C:23]([O:25][CH3:26])=[O:24])[CH2:21][CH2:20][N:13]1[C:11]([O:10][CH2:7][CH:8]=[CH2:9])=[O:12]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10957576HCID 10957576, compoundHCID 23665647Potassium tert-butoxideHCID 23672064Monosodium phosphate

Product 2

HCID 10923105HCID 10923105, compoundHCID 11076469HCID 11076469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of potassium tert-butoxide (3.42 g, 30 mol) in THF which was warmed at 60° C. was added a solution of methyl N-[(allyloxy)carbonyl]-N-(4-ethoxy-4-oxobutyl)-L-alaninate(4.60 g, 15 mmol) in THF (30 ml) and after stirring for 1 minute, the reaction solution was poured into an aqueous sodium dihydrogenphosphate solution (1M, 50 ml). The solution was adjusted to pH 2–3 and thereto was added ethyl acetate. After separating the mixture with a separating funnel, the aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography to give 1-allyl 4-ethyl (2S)-2-methyl-3-oxo-1,4-piperidinedicarboxylate (2.03 g) and 1-allyl 4-methyl (2S)-2-methyl-3-oxo-1,4-piperidinedicarboxylate (1.20 g).

Workup

  1. customAfter separating the mixture with a separating funnel
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe organic solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-787b61b5f52b4f358551e640550e5652
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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