Reaction equation
[CH2:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:3](=[O:10])[NH:2]1.Cl.O1CCOCC1>O=[Pt]=O.CC(O)=O>[CH2:1]1[CH:9]2[CH:4]([CH2:5][NH:6][CH2:7][CH2:8]2)[C:3](=[O:10])[NH:2]1Participants
Procedure
1,2-dihydro-3H-pyrrolo[3,4-c]pyridine-3-one (19.6 g, 0.146 mol) was placed into a hydrogenation reactor together with 250 mL AcOH and 1 g of PtO2 (Colonial Metals). An H2 pressure of 60 PSI was applied and the mixture hydrogenated until a pressure of 26 PSI was measured. The reaction mixture was filtered and the solvent evaporated. At the end of the evaporation, 4 N HCl in 1,4-dioxane (50 mL, 0.2 mol) was added. The solvent was evaporated to dryness. Ether (800 mL) was added and the mixture was stirred and filtered. The filter, a white solid, was dried to give 28.3 g of the desired product. 1H NMR (300 MHz, d6-DMSO) δ=9.42 (br s, 1H), 8.33 (br s, 1H), 7.88 (s, 1H), 3.44-3.25 (m, overlaps with water peak, observed integral of 6H includes water), 3.11-3.01 (m, 2H), 2.88-2.76 (m, 2H), 2.64 (br t, 1H), 2.55-2.45 (m, 3H) 1.90-1.75 (m, 1H), 1.61-1.42 (m, 1H). LCMS: 1.0 min, M+H=144.1 u/e.
Workup
- filtrationThe reaction mixture was filtered
- customthe solvent evaporated
- additionwas added
- customThe solvent was evaporated to dryness
- additionEther (800 mL) was added
- filtrationfiltered
- customThe filter, a white solid, was dried
Sources & evidence
- ORD record
- ord-254d064c0ab44d64b0d0d69eecedf2e6
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07468375B2
Linked notes
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