Acetone → 5,6-Dihydroxy-2-thiabicyclo[2.2.2]octan-3-one O-[(methylamino)carbonyl]oxime
Reaction equation
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]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
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.
Workup
- stirringAfter being stirred for 30 minutes
- filtrationthe mixture was filtered
- extractionThe filtrate was extracted with ethyl acetate
- customEvaporation of the dried organic solution
Sources & evidence
- ORD record
- ord-0f027d10c8fc40e7ad6cfca59e58188b
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04424213
Reaction notes
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