Tetrahydrofuran → HCID 22175856, compound

HRID 1797579Notes

Reaction equation

HRID 1797579 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]([CH:24]=[O:25])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].O1CCC[CH2:33]1>[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][C:28]([CH3:30])([CH3:33])[CH3:29])[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)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 22175412HCID 22175412, compound

Product 1

HCID 22175856HCID 22175856, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

To a solution of tert-butyl(4-butoxy-2-cyclopropylmethyl-6-formyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (2.27 g, 6.2 mmol) in tetrahydrofuran (30 mL) was added manganese dioxide (8.1 g) and the mixture was stirred at room temperature for 12 h. Manganese dioxide was filtered off and the mother liquor was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl(4-butoxy-6-formyl-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (2.52 g, 91.6%) as crystals.

Workup

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

Sources & evidence

ORD record
ord-3e12a03aaec84a62a5fb6d5102b6e576
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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