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

HRID 846745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846745
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 petroleumether. 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 petroleumether
  10. customThe latter was separated
  11. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-67b7f05b843a4f73bfb1f109cce23913
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137896

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