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

HRID 73492

반응식

HRID 73492 반응식
[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

참가 물질

8

반응물 2

HCID 962WaterHCID 67022378acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester2회

생성물 1

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

시약·촉매·용매 5

HCID 23994Zinc촉매HCID 165397Cupric acetate monohydrate촉매HCID 10290809Zinc copper couple촉매HCID 176Acetic Acid용매2회HCID 702Ethanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47b5b46af7d641bfb05f3897cfd12577
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829189B2

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