2-Pyridinesulfonic acid → 1-(Diphenylmethyl)azetidin-3-one

HRID 1437233

Reaktionsgleichung

Reaktionsgleichung von HRID 1437233
N1C=CC=CC=1S(O)(=O)=O.[CH:11]([N:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O.C(N(CC)CC)C>[CH:11]([N:24]1[CH2:27][C:26](=[O:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

5

Edukt 2

HCID 948492-Pyridinesulfonic acidHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Produkt 1

HCID 37355581-(Diphenylmethyl)azetidin-3-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Under cooling with ice, pyridinesulfonic acid (19.7 g) in dimethyl sulfoxide (84 mL) was added dropwise to 1-benzhydrylazetidin-3-ol (4.79 g) in triethylamine (27.9 mL), and the resultant mixture was stirred at 50° C. for 40 minutes. The reaction mixture was partitioned between ice-water and ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid (2.85 g, 60%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ice-water and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydrate
  4. filtrationfollowed by filtration
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-84f5b0b21cc84cbdb8c31f0d43e7a4d2
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622471B2

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