HCID 76724135, compound → 6,7-Dihydro-5H-cyclopenta[b]pyridin-5-amine

HRID 1818026Notes

Reaction equation

HRID 1818026 reaction equation
CO[N:3]=[C:4]1[CH2:12][CH2:11][C:10]2[N:9]=[CH:8][CH:7]=[CH:6][C:5]1=2>C(O)(C(F)(F)F)=O.[Pd]>[N:9]1[C:10]2[CH2:11][CH2:12][CH:4]([NH2:3])[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 76724135HCID 76724135, compound

Product 1

HCID 221473916,7-Dihydro-5H-cyclopenta[b]pyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6,7-dihydro-[1]pyrindin-5-one O-methyl-oxime (5.43 g, 33.5 mmol) and Pd/C (150 mg) in TFA were hydrogenated under 50 psi for 14 hours. Filtration via celite and concentration afforded the title amine. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 1.66-1.77 (m, 2H), 2.17-2.27 (m, 2H), 2.45-2.50 (m, 1H), 3.24-3.33 (m, 2H), 8.42-8.58 (m, 1H), 8.61-8.72 (m, 1H), 9.37-9.50 (m, 1H).

Workup

  1. filtrationFiltration
  2. concentrationvia celite and concentration

Sources & evidence

ORD record
ord-6b74c02545434a4598aed4f121952652
Source dataset
uspto-grants-2009_10
Patent number
US07598417B2

Reaction notes

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