5-(2-(Tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid → Tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate

HRID 1803215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803215
[C:1]([O:5][C:6]([NH:8][N:9]=[C:10]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:11][CH2:12][CH2:13][C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:15])[N:9]2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:18][CH:19]=1

Komponenten

4

Edukt 1

HCID 866499235-(2-(Tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid

Produkt 1

HCID 66859411Tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Step AAG (2): 10% Palladium on carbon (0.5 g) was carefully added to a solution of 5-(2-(tert-Butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid (2.3 g, 7.09 mmol) in MeOH (30 mL) in a Parr hydrogenation bottle under nitrogen. The bottle was repeatedly evacuated and flushed with H2 gas (50 psi). The mixture was shaken for 5 h. The vessel was flushed with nitrogen. The reaction contents were filtered through diatomaceous earth (Celite®). The plug and vessel were washed with fresh methanol. The filtrates were combined and concentrated in vacuo. The crude product was purified using silica gel column chromatography (10-80, EtOAc/chloroform, linear gradient) to afford tert-butyl 2-(4-fluorophenyl)-6-oxopiperidin-1-ylcarbamate (1.2 g, 55% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 7.13-7.20 (an, 2 H) 7.06 (t, J=8.55 Hz, 2 H) 6.40 (br. s., 1 H) 4.91 (br. s., 1 H) 2.52-2.75 (m, 2 H) 2.20-2.40 (m, 1 H) 1.77-1.93 (m, 3 H) 1.44 (s, 9 H).

Aufarbeitung

  1. customThe bottle was repeatedly evacuated
  2. customflushed with H2 gas (50 psi)
  3. customThe vessel was flushed with nitrogen
  4. customThe reaction contents
  5. filtrationwere filtered through diatomaceous earth (Celite®)
  6. washThe plug and vessel were washed with fresh methanol
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-2d753441dc3c47a698156e0846da5c66
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349880B2

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