Hydrazinecarboxaldehyde → (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine

HRID 397666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397666
[CH:1]([NH:3][NH2:4])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[C:21](=[NH:25])OCC)(=[O:14])=[O:13])=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.O1CCOCC1>[F:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[C:21]2[N:25]=[CH:1][NH:3][N:4]=2)(=[O:13])=[O:14])=[CH:10][CH:11]=1

Komponenten

5

Edukt 2

HCID 12229HydrazinecarboxaldehydeHCID 57097015ethyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboximidate

Produkt 1

HCID 178527361(2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidineAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Formylhydrazine (120 mg) was added to a solution of ethyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboximidate (295 mg) [see Preparation 41] in toluene (5 ml) and 1,4-dioxane (5 ml). The reaction mixture was stirred at reflux for 26 hours after which time the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate and washed with water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 0:100 (in 10% increments), by volume, hexane:ethyl acetate to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine (95 mg) as an off-white foam.

Aufarbeitung

  1. temperatureat reflux for 26 hours after which time the solvent
  2. customwas removed under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 0:100 (in 10% increments), by volume, hexane

Quellen und Nachweise

ORD-Eintrag
ord-1c9e22cef2ba480d9c6bc29238cd09e3
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610707B1

Notizen zur Reaktion

Wird geladen…