Sulfuric Acid → Ethyl [(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2,4-dioxopiperidin-1-yl]acetate

HRID 1866658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866658
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[C@@H:11]([OH:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.OS(O)(=O)=O>CC(C)=O.O.[O-2].[O-2].[O-2].[Cr+6]>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[C:11](=[O:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

6

Edukt 2

HCID 1118Sulfuric AcidHCID 86616394HCID 86616394, Verbindung2×

Produkt 1

HCID 86616396Ethyl [(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2,4-dioxopiperidin-1-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10219390chromium (VI) trioxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl [(4S,6S)-6-(3,5-difluorophenyl)-4-hydroxy-3,3-dimethyl-2-oxopiperidin-1-yl]acetate (470 mg, 1.377 mmol, described in Intermediate 21) in acetone (24 mL) at 0° C. was added a solution of chromium (VI) trioxide (174 mg, 1.740 mmol) in H2O (0.5 mL) and H2SO4 (0.147 mL, 2.75 mmol), in three portions over 5 min and the mixture was stirred at 0° C. for 30 min. Most of the acetone was removed by concentration in vacuo, and the residue was basified with saturated aqueous NaHCO3 (75 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (40 mL) and dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:CH3OH—100:0 to 92:8, to give the title compound. MS: m/z=340 (M+1).

Aufarbeitung

  1. customMost of the acetone was removed by concentration in vacuo
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with brine (40 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-69a7cdb2f6b54d1b9c9972eb3e664c66
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629338B2

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