HCID 70873118, compound → HCID 86680199, compound

HRID 2402354Notes

Reaction equation

HRID 2402354 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:15]2[CH2:18][CH2:17][CH2:16]2)([CH3:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[N+:19]([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:19][C:3]1[CH:4]=[C:5]([C:8]([CH:15]2[CH2:16][CH2:17][CH2:18]2)([CH3:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 70873118HCID 70873118, compound

Product 1

HCID 86680199HCID 86680199, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.79 g (5.74 mmol) of methyl 3-(4-chloro-3-nitrophenyl)-3-cyclobutylbutanoate were dissolved in 50 ml of ethyl acetate, and about 150 mg of 10% palladium on carbon were added. At RT, the reaction mixture was stirred vigorously under an atmosphere of hydrogen at atmospheric pressure overnight. The mixture was then filtered through Celite, and the filtrate obtained was evaporated to dryness. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave 1.36 g of the target product (84% of theory).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. customthe filtrate obtained
  3. customwas evaporated to dryness
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-4ee539dcbfa3443182f109b9e6a713b4
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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