Water → acetic acid (1RS,3RS,4RS)-4-amino-3-(3,4-dimethoxyphenyl)cyclohexyl ester

HRID 731686Notes

Reaction equation

HRID 731686 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]([N+:17]([O-])=O)[CH2:15][CH2:14][CH:13]([O:20][C:21](=[O:23])[CH3:22])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O>C(O)C.C(O)(=O)C.[Cu].[Zn].[Zn].O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[NH2:17][CH:16]1[CH2:15][CH2:14][CH:13]([O:20][C:21](=[O:23])[CH3:22])[CH2:12][CH:11]1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

8

Reactant 2

HCID 962WaterHCID 67022378acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester

Product 1

HCID 67022805acetic acid (1RS,3RS,4RS)-4-amino-3-(3,4-dimethoxyphenyl)cyclohexyl ester

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 165397Cupric acetate monohydrateCatalystHCID 10290809Zinc copper coupleCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Procedure

A solution of 10.37 g of acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester (compound G1) in 240 ml of ethanol is added to a zinc-copper couple, prepared from 16.8 g of zinc powder and 920 mg of copper (II) acetate monohydrate in acetic acid, the resulting suspension is refluxed and treated with 26 ml of acetic acid, 3.2 ml of water and 26 ml of ethanol. The resulting mixture is refluxed for further 15 min. The precipitate is filtered off with suction and the solvent is removed. Chromatographical purification on silica gel using a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 2/7/1 and concentration of the corresponding eluate fractions afford 5.13 g (55% of theory) of the title compound as a pale brown oil.

Workup

  1. temperaturethe resulting suspension is refluxed
  2. temperatureThe resulting mixture is refluxed for further 15 min
  3. filtrationThe precipitate is filtered off with suction
  4. customthe solvent is removed
  5. customChromatographical purification on silica gel using
  6. additiona mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 2/7/1 and concentration of the corresponding eluate fractions

Sources & evidence

ORD record
ord-4b6a24119f1d4b22bb2597ae5b5a52b4
Source dataset
uspto-grants-2009_09
Patent number
US07585872B2

Reaction notes

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