(+,-) 2-Phenyl-cyclopentanone oxime → Cyclopentanamine, 2-phenyl-, (1R,2R)-rel-

HRID 989480Notes

Reaction equation

HRID 989480 reaction equation
[C:1]1([CH:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[N:12]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 72517452(+,-) 2-Phenyl-cyclopentanone oxime

Product 1

HCID 10931745Cyclopentanamine, 2-phenyl-, (1R,2R)-rel-Yield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Scheme IA, step B: (+,−) 2-Phenyl-cyclopentanone oxime from preparation 6 above was dissolved in 35 mL of ethanol and hydrogenated using 90 mg of 5% Pd/C at 40° C. overnight at 413.69 kPa (60 psi). The solution was filtered and concentrated in vacuo to give 0.43 g (62%) of a colorless oil. Some dimeric material resulted by this procedure according to the mass spec. The cis:trans ratio was estimated to be 4:1. The amine was used directly without further purification. The NMR was consistent with the assigned structure.

Workup

  1. customat 40° C.
  2. customovernight
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d97089487d241f8ab90e0019bf8c2e7
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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