HCID 22175957, compound → HCID 22175412, compound

HRID 1797513Notes

Reaction equation

HRID 1797513 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[C:11](=[O:26])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([CH2:24][OH:25])=[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:31])[NH:7][CH2:8][C:9]1[N:10]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[C:11](=[O:26])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([CH:24]=[O:25])=[CH:14][CH:13]=2)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 22175957HCID 22175957, compound

Product 1

HCID 22175412HCID 22175412, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4 tert-butyl(4-butoxy-2-cyclopropylmethyl-6-hydroxymethyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.45 g, 3.5 mmol) in tetrahydrofuran (10 mL) was added manganese dioxide (0.12 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(4-butoxy-2-cyclopropylmethyl-6-formyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.33 g, 76.7%) 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-b846153e15e24ef0aa14239db90f53f5
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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