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

HRID 464645

反応式

HRID 464645 の反応式
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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6689a53c4f12421eb2d475620fde2eb4
出典データセット
uspto-grants-1985_10
特許番号
US04548929

関連ノート

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