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

HRID 73492

Reaktionsgleichung

Reaktionsgleichung von HRID 73492
[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

Komponenten

8

Edukt 2

HCID 962WaterHCID 67022378acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23994ZincKatalysatorHCID 165397Cupric acetate monohydrateKatalysatorHCID 10290809Zinc copper coupleKatalysatorHCID 176Acetic AcidLösungsmittel2×HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 10.37 g of acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester (compound C2) 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-47b5b46af7d641bfb05f3897cfd12577
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829189B2

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