Water → HCID 15656880, compound

HRID 2396011Notes

Reaction equation

HRID 2396011 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([N:9]1[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19][CH3:20])[C:10]1=[O:21])[CH2:2]2.[H][H].O>CO.[Pd]>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@H:3]([N:9]1[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19][CH3:20])[C:10]1=[O:21])[CH2:2]2

Participants

6

Reactant 3

HCID 962WaterHCID 15656872HCID 15656872, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15656880HCID 15656880, compoundYield 112%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-2-(1-Azabicyclo[2.2.2]oct-3-yl)-5-ethyl-1(2H)-isoquinolinone (0.49 g, 1.5 mmol), from Example 2, was dissolved in methanol (10 ml) and reduced with hydrogen and 10% palladium on carbon at 50 psi for 5 hours. Filtration to remove the catalyst and evaporation of the methanol gave (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-5-ethyl-3,4-dihydro-1(2H)-isoquinolinone (0.48 g, 1.68 mmol), m.p. >290° C., [α]D25 -40.3° (c=0.64 H2O ).

Workup

  1. filtrationFiltration
  2. customto remove
  3. customthe catalyst and evaporation of the methanol

Sources & evidence

ORD record
ord-88d4cf78ea304cfe8998a094f7637242
Source dataset
uspto-grants-1996_02
Patent number
US05491148

Reaction notes

Loading…