HCID 131724336, compound → HCID 131724337, compound

HRID 2119984Notes

Reaction equation

HRID 2119984 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-])=O)[O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])[O:8][Si:9]([CH3:10])([CH3:11])[CH3:12])[CH3:2]

Participants

4

Reactant 1

HCID 131724336HCID 131724336, compound

Product 1

HCID 131724337HCID 131724337, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(2-nitro-phenyl)-4-trimethlysilanyloxy-butyric acid ethyl ester (200 mg, 0.6 mmol) in dry EtOAc (5 mL) was hydrogenated (1 atm) in the presence of Pd/C (20 mg) overnight Then the mixture was filtered and evaporated. The residue was dissolve in dry MeOH (5 mL) and was further hydrogenated (1 atm) in the presence of Pd/C (20 mg) for 1 h. The mixture was then filtered and the filtrate evaporated. Purification of this residue by filtration over silica gel, eluting with hexane: ethyl acetate (8:1) afforded the title compound (130 mg, 72%) as a colorless oil; m/z 295 (M).

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolve in dry MeOH (5 mL)
  4. customfor 1 h
  5. filtrationThe mixture was then filtered
  6. customthe filtrate evaporated
  7. customPurification of this residue
  8. filtrationby filtration over silica gel
  9. washeluting with hexane: ethyl acetate (8:1)

Sources & evidence

ORD record
ord-102edcbbae1c46e2955778d7a6b6fad7
Source dataset
uspto-grants-2004_02
Patent number
US06686352B2

Reaction notes

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