Cornforth reagent → (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxaldehyde

HRID 432828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432828
C([C@H:3]1[CH:8]([CH2:9][OH:10])[CH2:7][CH2:6][CH2:5][N:4]1[C:11](=[O:18])[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)C.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][C:11]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:8]([CH:9]=[O:10])[CH2:3]1)=[O:18]

Komponenten

4

Edukt 2

HCID 2724130Cornforth reagentHCID 86759306(S)-ethyl 1-(2-thiopheneacetyl)-3-hydroxymethylpiperidine

Produkt 1

HCID 28271707(S)-1-(2-thiopheneacetyl)-3-piperidinecarboxaldehydeAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-ethyl 1-(2-thiopheneacetyl)-3-hydroxymethylpiperidine (180.4 ml; 0.75 mmol) was dissolved in dichloromethane (20 ml). Crushed molecular sieves (0.25 g), and commercially available pyridinium dichromate (331.2 mg; 0.88 mmol) were added and the mixture was allowed to stir at ambient temperature for 5 hours. The mixture was then filtered through celite, washed with decolorizing carbon, filtered again and then evaporated under reduced pressure at ambient temperature. Crude product was purified by distillation at approximately 250° C./0.1 torr, giving (S)-1-(2-thiopheneacetyl)-3-piperidinecarboxaldehyde (58 mg) as a thick colorless oil. MS m/z (positive ion) 317 (25), 238 (MH+; 100).

Aufarbeitung

  1. additionwere added
  2. filtrationThe mixture was then filtered through celite
  3. washwashed with decolorizing carbon
  4. filtrationfiltered again
  5. customevaporated under reduced pressure at ambient temperature
  6. distillationCrude product was purified by distillation at approximately 250° C./0.1 torr

Quellen und Nachweise

ORD-Eintrag
ord-371169213b284b818385f33124448ed9
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664271B1

Notizen zur Reaktion

Wird geladen…