Tetrahydrofuran → HCID 53811755, compound

HRID 260454Notes

Reaction equation

HRID 260454 reaction equation
[CH2:1]([O:3][C:4](=[O:27])/[CH:5]=[CH:6]/[C:7]1[N:8]([CH3:26])[C:9](=[O:25])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][C:13]([CH3:23])=[C:12]([CH3:24])[CH:11]=2)[CH3:2].C1COCC1>[C].[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][C:7]1[N:8]([CH3:26])[C:9](=[O:25])[C:10]2[C:15]([C:16]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:14][C:13]([CH3:23])=[C:12]([CH3:24])[CH:11]=2)[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67734382HCID 67734382, compound

Product 1

HCID 53811755HCID 53811755, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of the compound (1.0 g) obtained in Step 2, 10% palladium-carbon (300 mg), THF (15 ml) and ethanol (15 ml) was stirred for 1.5 hours at room temperature under hydrogen atmosphere. The catalyst was filtered off. From the filtrate was distilled off the solvent. The residue was dissolved in ethyl acetate, which was washed with 2N-HCl, an aqueous solution of sodium hydrogencarbonate and water, successively, followed by drying (MgSO4). The solvent was distilled off to leave 3-(1,2-dihydro-2,6,7-trimethyl-1-oxo-4-phenylisoquinolin-3-yl)propionic acid ethyl ester as colorless crystals (0.85 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationFrom the filtrate was distilled off the solvent
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwhich was washed with 2N-HCl
  5. dry with materialby drying (MgSO4)
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-d89db9b850924d5eab59bb3814562a58
Source dataset
uspto-grants-1996_06
Patent number
US05527811

Reaction notes

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