Acetone → HCID 69363153, compound

HRID 2216356Notes

Reaction equation

HRID 2216356 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[CH2:5]([C:12]1[CH:13]=[C:14]([N:18]2[CH2:22]C=CC2)[CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C[N+]1([O-])CC[O:27]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.C(O)(C)(C)C.O>[CH2:5]([C:12]1[CH:13]=[C:14]([N:18]2[CH2:4][C@H:2]([OH:3])[C@H:1]([OH:27])[CH2:22]2)[CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 219423032,5-Dihydro-1-[3-(phenylmethyl)phenyl]-1H-pyrrole

Product 1

HCID 69363153HCID 69363153, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

While stirring 20 ml of an acetone solution of 2.1 g of 1-(3-benzylphenyl)-2,5-dihydropyrrole on an ice bath, 2.2 ml of a 50% aqueous solution of N-methylmorpholine-N-oxide, 4 ml of water and 0.5 ml of a 2.5% t-butanol solution of osmium tetroxide were successively added thereto, followed by stirring as it was at room temperature overnight. After adding 2 ml of a 1 M aqueous solution of sodium thiosulfate, the reaction mixture was extracted with ethyl acetate-water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography with 10–50% ethyl acetate/hexane, to give 1.15 g of the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate-water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography with 10–50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-926742a0f93448b1a458be938f281334
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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