Acetic Acid → 2-Diethoxyphosphoryl-1-[1-(4-methyl-2-pyridyl)-4-piperidyl]ethanone

HRID 1775352

Reaktionsgleichung

Reaktionsgleichung von HRID 1775352
[CH3:1][P:2](=[O:9])([O:6][CH2:7][CH3:8])[O:3][CH2:4][CH3:5].C([Li])CCC.[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([N:22]2[CH2:27][CH2:26][CH:25]([C:28](OCC)=[O:29])[CH2:24][CH2:23]2)[CH:17]=1.C(O)(=O)C>C1COCC1>[CH2:4]([O:3][P:2]([CH2:1][C:28]([CH:25]1[CH2:26][CH2:27][N:22]([C:18]2[CH:17]=[C:16]([CH3:15])[CH:21]=[CH:20][N:19]=2)[CH2:23][CH2:24]1)=[O:29])([O:6][CH2:7][CH3:8])=[O:9])[CH3:5]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 12685Diethyl methylphosphonateHCID 62007359Ethyl 1-(4-methyl-2-pyridyl)piperidine-4-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 898258172-Diethoxyphosphoryl-1-[1-(4-methyl-2-pyridyl)-4-piperidyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Diethyl methylphosphonate (1.27 g, 8.36 mmol) was dissolved in anhydrous THF (7 ml), the solution was purged with argon and cooled to −78° C. n-Butyllithium (2M in hexane, 2.67 ml, 5.34 mmol) was added at such a rate that the temperature remained below −65° C. After addition was complete, stirring was continued for 20 minutes, then a solution of ethyl 1-(4-methyl-2-pyridyl)piperidine-4-carboxylate (626 mg, 2.52 mmol) in anhydrous THF (1 ml) was added dropwise so that the temperature remained below −70° C. Stirring was continued overnight while the temperature was allowed to reach room temperature. The mixture was neutralized with glacial acetic acid, concentrated under reduced pressure, water was added and the mixture was extracted with DCM (3×). The combined organic phases were dried (sodium sulfate), and concentrated under reduced pressure to give a brown oil that was used directly in the next step MS (multi-mode) m/z=355.1 [M+1]+.

Aufarbeitung

  1. customthe solution was purged with argon
  2. additionwas added at such a rate that the temperature
  3. customremained below −65° C
  4. additionAfter addition
  5. customremained below −70° C
  6. stirringStirring
  7. waitwas continued overnight while the temperature
  8. customto reach room temperature
  9. concentrationconcentrated under reduced pressure, water
  10. additionwas added
  11. extractionthe mixture was extracted with DCM (3×)
  12. dry with materialThe combined organic phases were dried (sodium sulfate)
  13. concentrationconcentrated under reduced pressure
  14. customto give a brown oil that

Quellen und Nachweise

ORD-Eintrag
ord-f37bccb58b9c4b7282698af3d7970317
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260441B2

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