HCID 69031216, compound → HCID 11593606, compound

HRID 2218568Notes

Reaction equation

HRID 2218568 reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[N:17]1[CH2:21][CH:20]([CH3:22])[CH2:19][C:18]1=[O:23])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH2:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[N:17]1[CH2:21][CH:20]([CH3:22])[CH2:19][C:18]1=[O:23]

Participants

5

Reactant 2

HCID 69031216HCID 69031216, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11593606HCID 11593606, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of trans-[2-(4-methyl-2-oxo-pyrrolidin-1-yl)-cydohexyl]-carbamic acid benzyl ester (34 mg) in absolute ethanol (4.0 ml) was added 10% Pd on charcoal (5 mg). A hydrogen atmosphere was introduced by repeated evacuation/gas introduction. The suspension was vigorously stirred over night. The catalyst was removed by filtration through dicalite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 93/7/0.5) to give the product as a 1:1 mixture of epimers as a colorless liquid (15 mg). MS (ESI): 197.3 (M+H+).

Workup

  1. customThe catalyst was removed by filtration through dicalite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 93/7/0.5)
  4. customto give the product

Sources & evidence

ORD record
ord-4f55a37b36c54e8aa898c5d0da317302
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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