(5-Nitro-1-cyclopentenyl)benzene → Cyclopentanamine, 2-phenyl-, (1R,2R)-rel-

HRID 989478Notes

Reaction equation

HRID 989478 reaction equation
[N+:1]([CH:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH2:6][CH2:5]1)([O-])=O>C(O)C.[Pd]>[C:9]1([C@H:8]2[CH2:7][CH2:6][CH2:5][C@H:4]2[NH2:1])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 18006301(5-Nitro-1-cyclopentenyl)benzene

Product 1

HCID 10931745Cyclopentanamine, 2-phenyl-, (1R,2R)-rel-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(5-Nitro-cyclopent-1-enyl)-benzene (0.63 g, 3.3 mmol) from preparation 4 above, was hydrogenated in 25 mL of ethanol using 0.16 g of 5% Pd/C at room temperature overnight at 413.69 kPa (60 psi). The solution was filtered over celite and concentrated in vacuo to 230 mg (43%) of the title compound as a colorless oil. The NMR was consistent with the assigned structure. Mass Spectrum (ES MS): M+1=162.

Workup

  1. filtrationThe solution was filtered over celite and
  2. concentrationconcentrated in vacuo to 230 mg (43%) of the title compound as a colorless oil

Sources & evidence

ORD record
ord-b6525b6a5a85433a8e7bd13c4db34c95
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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