Sodium periodate → 15991-93-2

HRID 1587023Notes

Reaction equation

HRID 1587023 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][C@H:17]([O:24][C:25](=[O:27])[CH3:26])[C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:28](=[CH2:44])CC=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6]1)(=[O:3])[CH3:2].I([O-])(=O)(=O)=[O:46].[Na+]>C(Cl)(Cl)(Cl)Cl.C(#N)C.O.C(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[C:28]([C@H:14]1[CH2:13][CH2:12][C@H:11]2[C@H:10]3[C@H:19]([CH2:18][C@H:17]([O:24][C:25](=[O:27])[CH3:26])[C@:15]12[CH3:16])[C@:20]1([CH3:23])[C@@H:7]([CH2:6][C@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:22][CH2:21]1)[CH2:8][CH2:9]3)(=[O:46])[CH3:44]

Participants

8

Reactant 2

HCID 23667635Sodium periodate2×HCID 86746917HCID 86746917, compound

Product 1

HCID 1195414215991-93-2

Reagents, catalysts & solvents 5

HCID 6093376Ruthenium trichloride hydrateCatalyst2×HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude 3α, 12α-diacetoxy-17β-[(1,1-diphenyl)-1,4-pentadien-4-yl]-5β-androstane (43.6 g) in carbon tetrachloride (110 ml), acetonitrile (110 ml) and water (146 ml) is added sodium periodate (46.8 g) and ruthenium(III) chloride hydrate (0.373 g). The mixture is stirred vigorously at room temperature for about 1 hour, sodium periodate (5.0 g) and ruthenium(III) chloride hydrate (0.10 g) are added and stirring continued for about 30 minutes. The mixture is diluted with methylene chloride, washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography in 5% ether in methylene chloride and further purified by flash chromatography in 25% ethyl acetate in hexane to give the desired product.

Workup

  1. stirringstirring
  2. waitcontinued for about 30 minutes
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash chromatography in 5% ether in methylene chloride
  8. customfurther purified by flash chromatography in 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-91a88b0a4e1247d4a39406957e057a18
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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