Sulfuric Acid → Ethyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylate

HRID 1088352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088352
C[O:2][C:3]1(OC)[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH:4]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)O>O>[O:2]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH:4]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 3019743Ethyl 4,4-dimethoxy-3-(phenylmethoxy)piperidine-1-carboxylate

Produkt 1

HCID 3019711Ethyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 94 parts of ethyl 4,4-dimethoxy-3-(phenylmethoxy)-1-piperidinecarboxylate and 2300 parts of a sulfuric acid solution 1% in water was stirred and refluxed for 2.50 hours. The reaction mixture was cooled and the product was extracted three times with dichloromethane. The combined extracts were washed with a small amount of water, dried, filtered and evaporated. The residue was taken up in methylbenzene and the latter was evaporated again. The residue was stirred in petroleum ether. The latter was separated and the solvent was evaporated, yielding 64.9 parts of ethyl 4-oxo-3-(phenylmethoxy)-1-piperidinecarboxylate as a residue (intermediate 50).

Aufarbeitung

  1. temperaturerefluxed for 2.50 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe product was extracted three times with dichloromethane
  4. washThe combined extracts were washed with a small amount of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customthe latter was evaporated again
  9. stirringThe residue was stirred in petroleum ether
  10. customThe latter was separated
  11. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d4c82bf49a374db8acca0e07991709fc
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04962115

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