HCID 67151589, compound → HCID 67151663, compound

HRID 1805235Notes

Reaction equation

HRID 1805235 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C@H:12]2[CH2:16][O:15][C:14]([NH2:17])=[N:13]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C@H:12]2[CH2:16][O:15][C:14]([NH2:17])=[N:13]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 67151589HCID 67151589, compound

Product 1

HCID 67151663HCID 67151663, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-4-[(E)-2-(4-Nitro-phenyl)-vinyl]-4,5-dihydro-oxazol-2-ylamine (0.95 g) was dissolved in methanol (40 ml) before addition of Pd/C 10% (95 mg). The reaction mixture was hydrogenated for 1 hour at room temperature and then the catalyst was filtered off and washed with methanol. The residue was concentrated in vacuo and purified by Isco chromatography (column: Silicycle Si-Amine, AcOEt) to afford (S)-4-[2-(4-amino-phenyl)-ethyl]-4,5-dihydro-oxazol-2-ylamine (800 mg) as an off-white solid. MS (ISP): 206.2 ([M+H]+).

Workup

  1. filtrationthe catalyst was filtered off
  2. washwashed with methanol
  3. concentrationThe residue was concentrated in vacuo
  4. custompurified by Isco chromatography (column: Silicycle Si-Amine, AcOEt)

Sources & evidence

ORD record
ord-0226de0421ca4aa6950f699039284cf1
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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