HCID 9815533, compound → HCID 9837040, compound

HRID 2296628Notes

Reaction equation

HRID 2296628 reaction equation
[CH2:1]([CH:4]1[N:10]2[C:11](=[O:14])[O:12][N:13]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=C.I([O-])(=O)(=O)=[O:16].[Na+]>O1CCOCC1.O.CCCCO.O.[Os](=O)(=O)(=O)=O.[Os](=O)=O>[O:14]=[C:11]1[N:10]2[CH:4]([CH2:1][CH:2]=[O:16])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]2=[N:13][O:12]1

Participants

8

Reactant 2

HCID 9815533HCID 9815533, compoundHCID 23667635Sodium periodate

Product 1

HCID 9837040HCID 9837040, compoundYield 67%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalyst2×HCID 18757412036-02-1CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 22253497Water butanolSolvent

Procedure

To a solution of the product of Example 6 in dioxane (200 mL) and water (135 mL) was added sodium periodate (15.11 g, 0.071 mol) and osmium tetraoxide (12 drops of a 1 ppm solution of osmium dioxide in n-BuOH/H2O). The reaction was stirred at room temperature and monitor by thin layer chromatography for one day. Since the starting material had not completely reacted, additional osmium tetraoxide (12 drops of 1 ppm solution of osmium dioxide in n-BuOH/H2O) was added. A white precipitate was filtered off and the filtrate was removed under reduced pressure to the point where no dioxane remained. Additional water (75 mL) was then added to the aqueous layer and this aqueous mixture was washed with CH2Cl2 (3×75 mL). The organic layer was combined, dried over magnesium sulfate, and stripped of all solvent under reduced pressure to afford a yellow oil. Chromatographic (silica gel) purification of this material eluting with the 1:1, ethyl acetate:hexane afforded 4.0 g (67%) of the title compound. 1H NMR (CDCl3, 300 MHz) d 1.2-2.5 (m, 6H), 2.59 (q, 2H), 2.92 (m, 2H), 4.79 (m, 1H), 9.79 (ss, 1H). 13C NMR (CDCl3, 75 MHz) d 24.12, 31.52, 32.00, 45.61, 49.10, 53.98, 159.9, 160.8, 198.1.

Workup

  1. customSince the starting material had not completely reacted
  2. filtrationA white precipitate was filtered off
  3. customthe filtrate was removed under reduced pressure to the point where no dioxane
  4. additionAdditional water (75 mL) was then added to the aqueous layer
  5. washthis aqueous mixture was washed with CH2Cl2 (3×75 mL)
  6. dry with materialdried over magnesium sulfate
  7. customto afford a yellow oil
  8. customChromatographic (silica gel) purification of this material
  9. washeluting with the 1:1, ethyl acetate

Sources & evidence

ORD record
ord-1e776af949f5466896487519b2979448
Source dataset
uspto-grants-2002_12
Patent number
US06489323B1

Reaction notes

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