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

HRID 2054433Notes

Reaction equation

HRID 2054433 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 ester2×

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 C1) 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/triethyl-amine 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/triethyl-amine in the ratio 2/7/1 and concentration of the corresponding eluate fractions

Sources & evidence

ORD record
ord-dc6f5dd100bd4651b07eedb6482edbca
Source dataset
uspto-grants-2008_02
Patent number
US07329676B2

Reaction notes

Loading…