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

HRID 464645

반응식

HRID 464645 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6689a53c4f12421eb2d475620fde2eb4
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548929

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