HCID 86605650, compound → HCID 86605665, compound

HRID 1986501Notes

Reaction equation

HRID 1986501 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:7]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH:2]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:7]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)=[O:1]

Participants

4

Reactant 1

HCID 86605650HCID 86605650, compound

Product 1

HCID 86605665HCID 86605665, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl [6-(hydroxymethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (0.46 g, 1.1 mmol), manganese dioxide (chemically treated product, 1.4 g, 16 mmol) and tetrahydrofuran (20 ml) was stirred at room temperature for 12 hrs. The reaction mixture was filtered, and the filtrate was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give tert-butyl [6-formyl-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (0.28 g, yield 62%) as a white powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5a090bcc647f4bc9a81d119269358e22
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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