HCID 59834881, compound → HCID 59834905, compound

HRID 271372Notes

Reaction equation

HRID 271372 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C@H:11]2[CH2:15][CH2:14][C@H:13]([NH:16]C(=O)OCC3C=CC=CC=3)[CH2:12]2)=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][C@H:11]2[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 59834881HCID 59834881, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59834905HCID 59834905, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl {trans-3-[2-(4-methylphenyl)ethoxy]cyclopentyl}carbamate (291 mg, 0.82 g) and 5% palladium on carbon (150 mg) in ethanol (8 ml) was hydrogenated (hydrogen balloon) for three hours. The catalyst was removed by filtration through Celite. The filter cake was washed with ethanol (3×10 ml) and the filtrate was concentrated under reduced pressure to give an oil. The oil was filtered through a pad of silica gel eluting first with methanol: methylene chloride (10:90) to remove impurities, then with methanol: methylene chloride: conc. ammonium hydroxide (20:80:2), and the filtrate concentrated to give trans-3-[2-(4-methylphenyl)ethoxy]cyclopentanamine (154 mg, 86%), as a colorless oil.

Workup

  1. customfor three hours
  2. customThe catalyst was removed by filtration through Celite
  3. washThe filter cake was washed with ethanol (3×10 ml)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give an oil
  6. filtrationThe oil was filtered through a pad of silica gel eluting first with methanol: methylene chloride (10:90)
  7. customto remove impurities
  8. concentrationwith methanol: methylene chloride: conc. ammonium hydroxide (20:80:2), and the filtrate concentrated

Sources & evidence

ORD record
ord-a5fa6014c28a41348281a66281403752
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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