Potassium Carbonate → (S)-tert-butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407879
CS([O:5][C@@H:6]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:7]1=[O:24])(=O)=O.[Br:25][C:26]1[CH:31]=[CH:30][C:29](O)=[C:28]([F:33])[CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([O:5][C@H:6]2[CH2:10][CH2:9][N:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:7]2=[O:24])=[C:28]([F:33])[CH:27]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 86688072(R)-tert-butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 86688077(S)-tert-butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(R)-tert-Butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (Preparation D; 1.7 g, 4.7 mmol) was dissolved in dry DMSO (30 mL) and 4-bromo-2-fluorophenol (1.1 g, 5.6 mmol) and K2CO3 (0.78 g, 5.6 mmol) was added and the reaction heated to 70° C. under nitrogen. The reaction became purple then black. The reaction was cooled to ambient temperature after 3 hours and partitioned between water and EtOAc, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (40% EtOAc in hexanes) to afford (S)-tert-butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (1.8 g, 3.9 mmol, 84% yield) as a white solid.

Aufarbeitung

  1. temperatureThe reaction was cooled to ambient temperature after 3 hours
  2. custompartitioned between water and EtOAc
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified over silica gel (40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7f141bf48955487790f07a31bf7c3e3f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754226B2

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