Acetone → 5,6-Dihydroxy-2-thiabicyclo[2.2.2]octan-3-one O-[(methylamino)carbonyl]oxime

HRID 464645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464645
C[N+]1([O-])CC[O:5]CC1.[CH3:9][NH:10][C:11]([O:13][N:14]=[C:15]1C2CC[CH:17]([CH:18]=[CH:19]2)[S:16]1)=[O:12].S(=O)(O)[O-].[Na+].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2].[CH3:35][C:36]([CH3:38])=[O:37]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O.O>[CH3:9][NH:10][C:11]([O:13][N:14]=[C:15]1[CH:38]2[CH2:19][CH2:18][CH:17]([CH:35]([OH:5])[CH:36]2[OH:37])[S:16]1)=[O:12]

Komponenten

9

Edukt 5

HCID 180AcetoneHCID 66225Magnesium orthosilicateHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 543231632-thiabicyclo[2.2.2]oct-5-en-3-one O-[(methylamino)carbonyl]oxime

Produkt 1

HCID 540124775,6-Dihydroxy-2-thiabicyclo[2.2.2]octan-3-one O-[(methylamino)carbonyl]oxime

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a solution of 6.5 g (0.048 m) of N-methylmorpholine N-oxide and 5.0 g (0.024 m) of 2-thiabicyclo[2.2.2]oct-5-en-3-one O-[(methylamino)carbonyl]oxime in 20 ml of acetone was added 15 ml of a 0.5% solution of osmium tetroxide in tert-butanol. The reaction mixture was stirred at room temperature for 48 hours, then treated with a slurry of 1 g sodium bisulfite, 15 g of magnesium silicate, and 50 ml of water. After being stirred for 30 minutes, the mixture was filtered. The filtrate was extracted with ethyl acetate, then with methylene chloride. Evaporation of the dried organic solution gave 4.8 g of viscous oil. Purification by dry column chromatography yielded 3.5 g of the title compound as a white solid, m. 123°-5° C.

Aufarbeitung

  1. stirringAfter being stirred for 30 minutes
  2. filtrationthe mixture was filtered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. customEvaporation of the dried organic solution

Quellen und Nachweise

ORD-Eintrag
ord-6689a53c4f12421eb2d475620fde2eb4
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04548929

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