HCID 22175460, compound → HCID 22175466, compound

HRID 1797563Notes

Reaction equation

HRID 1797563 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([CH2:25][OH:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([CH:25]=[O:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22175460HCID 22175460, compound

Product 1

HCID 22175466HCID 22175466, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl(6-hydroxymethyl-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (4.58 g, 10.5 mmol) in tetrahydrofuran (50 mL) was added manganese dioxide (13.7 g) and the mixture was stirred at room temperature for 12 h. Manganese dioxide was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl(6-formyl-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (4.12 g, 90.4%) as crystals.

Workup

  1. filtrationManganese dioxide was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0a50da6284e04240ae2b6fc5ff15d85c
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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