HCID 22175667, compound → HCID 22175869, compound

HRID 1797531Notes

Reaction equation

HRID 1797531 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][CH2:8][C:9]1[N:10]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:11](=[O:32])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([O:24]CC1C=CC=CC=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.C(O)C.[C].[Pd]>[CH2:20]([O:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:24])[CH:16]=2)[C:11](=[O:32])[N:10]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:9]=1[CH2:8][NH:7][C:6](=[O:37])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 1

HCID 22175667HCID 22175667, compound

Product 1

HCID 22175869HCID 22175869, compoundYield 96.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of tert-butyl(6-benzyloxy-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (6.10 g, 12 mmol) and 5% palladium carbon (2.0 g) in tetrahydrofuran (30 mL) and ethanol (30 mL) was stirred under a hydrogen atmosphere at room temperature for 2 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate-diisopropyl ether to give tert-butyl (4-butoxy-6-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (4.86 g, 96.8%) as crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-e2070dae8ca14929bbd39eaf3388600c
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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