HCID 68448458, compound → HCID 68446005, compound

HRID 2233194Notes

Reaction equation

HRID 2233194 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][CH2:7][C:6](=[O:12])[N:5]3[CH2:13][C:14]([OH:17])([CH2:15][OH:16])[C:3]=1[C:4]=23>CN(C=O)C.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6](=[O:12])[N:5]3[CH2:13][C:14]([OH:17])([CH2:15][OH:16])[C:3]=1[C:4]=23

Participants

4

Reactant 1

HCID 68448458HCID 68448458, compound

Product 1

HCID 68446005HCID 68446005, compoundYield 113%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-fluoro-6-hydroxy-6-(hydroxymethyl)-1,2,5,6-tetrahydro-3H-pyrrolo[1,2,3-de]quinoxalin-3-one (0.331 g, 0.001 mol), and manganese (IV) oxide (1.84 g, 0.021 mol) in DMF (50 mL) was stirred at room temperature for 1 hour. The reaction mixture was filtered through Celite®, washed with methanol and the solvent was removed. The residue was placed directly onto the top of a 20 g silica gel column and chromatographed, eluting with a 0-100% ethyl acetate in hexane gradient, then with a 0-50% methanol in ethyl acetate gradient to afford the product (0.267 g, 81%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashed with methanol
  3. customthe solvent was removed
  4. customchromatographed
  5. washeluting with a 0-100% ethyl acetate in hexane gradient

Sources & evidence

ORD record
ord-165a45952f344d818371101b435a378b
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

Loading…