HCID 22175901, compound → HCID 22175724, compound

HRID 1797590Notes

Reaction equation

HRID 1797590 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][CH2:8][C:9]1[N:10]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:11](=[O:35])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:16][C:15]([O:27]CC1C=CC=CC=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.C(O)C.[C].[Pd]>[C:1]([O:5][C:6](=[O:40])[NH:7][CH2:8][C:9]1[N:10]([CH2:36][CH:37]([CH3:38])[CH3:39])[C:11](=[O:35])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][C:23]([F:26])([F:24])[F:25])=[CH:16][C:15]([OH:27])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 22175901HCID 22175901, compound

Product 1

HCID 22175724HCID 22175724, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of tert-butyl[6-benzyloxy-2-isobutyl-1-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydro-3-isoquinolinyl]methylcarbamate (3.09 g, 5.5 mmol) and 5% palladium carbon (1.0 g) in tetrahydrofuran (20 mL) and ethanol (20 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 residue was purified by silica gel column chromatography to give tert-butyl[6-hydroxy-2-isobutyl-1-oxo-4-(4,4,4-trifluorobutoxy)-1,2-dihydro-3-isoquinolinyl]methylcarbamate (2.48 g, 95.4%) as crystals.

Workup

  1. filtrationThe catalyst 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-5f1394255e3946dbbc3622bf20a2a92b
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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