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

HRID 73492

反応式

HRID 73492 の反応式
[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

参加物

8

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 23994Zinc触媒HCID 165397Cupric acetate monohydrate触媒HCID 10290809Zinc copper couple触媒HCID 176Acetic Acid溶媒2 回HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47b5b46af7d641bfb05f3897cfd12577
出典データセット
uspto-grants-2014_09
特許番号
US08829189B2

関連ノート

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