(E)-5H-cyclopenta[b]pyridin-7(6H)-one O-methyl oxime → 6,7-dihydro-5H-cyclopenta(b)pyridin-7-amine

HRID 1818025Notes

Reaction equation

HRID 1818025 reaction equation
CO[N:3]=[C:4]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5]1>C(O)(C(F)(F)F)=O.[Pd]>[N:11]1[C:12]2[CH:4]([NH2:3])[CH2:5][CH2:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 76724134(E)-5H-cyclopenta[b]pyridin-7(6H)-one O-methyl oxime

Product 1

HCID 120990656,7-dihydro-5H-cyclopenta(b)pyridin-7-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

5,6-Dihydro-[1]pyrindin-7-one O-methyl-oxime (4.1 g, 25.28 mmol) and Pd/C (150 mg) were mixed in TFA and then resulting reaction mixture was hydrogenated under 50 psi for 14 hours. Filtration via celite and concentration afforded the desired title amine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 1.89-2.02 (m, 1H), 2.46-2.58 (m, 1H), 2.89-3.01 (m, 2H), 4.62-4.73 (m, 1H), 7.30-7.37 (m, 1H), 7.77 (d, J=7.62 Hz, 1H), 8.35-8.50 (m, 3H).

Workup

  1. customresulting
  2. customreaction mixture
  3. filtrationFiltration
  4. concentrationvia celite and concentration

Sources & evidence

ORD record
ord-e1ef9048c8c34e3ba2e6850413d976dc
Source dataset
uspto-grants-2009_10
Patent number
US07598417B2

Reaction notes

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