Water → HCID 69419644, compound

HRID 1375077Notes

Reaction equation

HRID 1375077 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O.[Cl-].[NH4+]>CO.[Fe]>[C:1]([O:5][C:6](=[O:22])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 69418545HCID 69418545, compound

Product 1

HCID 69419644HCID 69419644, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A stirred solution of [1-(4-nitro-phenyl)-cyclopentyl]-acetic acid tert-butyl ester [1.0 g, Reference Example 6(a)] in methanol (40 mL) was treated with water (40 mL), ammonium chloride (0.87 g) and iron powder (325 mesh, 0.55 g). The mixture was stirred at gentle reflux for 2.5 hours and then the hot mixture was filtered through hyflo. The filter pad was washed well with methanol. The combined filtrate and washings was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate and then evaporated to give the title compound (0.63 g) as a golden oil.

Workup

  1. temperatureat gentle reflux for 2.5 hours
  2. filtrationthe hot mixture was filtered through hyflo
  3. washThe filter pad was washed well with methanol
  4. customThe combined filtrate and washings was evaporated
  5. customthe residue was partitioned between ethyl acetate and water
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-b76ca4c23b494370b469226ae5c74d9a
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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