Homoveratrylamine → 8-[2-(3,4-Dimethoxyphenyl)ethyl]-8-azabicyclo[3.2.1]octane-3-one

HRID 727097ノート

反応式

HRID 727097 の反応式
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.[CH3:10][C:11]([CH3:13])=O.C(O)=O.C(O)=O.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][NH2:32])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C([O-])(=O)C.[Na+]>Cl>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][N:32]2[CH:6]3[CH2:5][CH2:13][CH:11]2[CH2:10][C:3](=[O:4])[CH2:7]3)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

参加物

6

反応物 4

HCID 8421HomoveratrylamineHCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 53400708Acetone dicarboxylic acid

生成物 1

HCID 152313198-[2-(3,4-Dimethoxyphenyl)ethyl]-8-azabicyclo[3.2.1]octane-3-one収率 66.9%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒2 回

反応条件

温度
10 °C

実験手順

Following a general procedure previously described (P. Doster et al. Eur. I. Med. Chem. 1984, 19, 105), 8.2 g (62 mmol) 2,5-dimethoxytetrahydrofuran were heated at 80° C. in 75 ml of 0.1N aqueous HCl for 1 h. After cooling to 10° C., 10 g (68.4 mmol) acetone dicarboxylic acid, 12.4 g (68.5 mmol) 2-(3,4-dimethoxyphenyl)ethylamine, 6.13 g (74.7 mmol) sodium acetate and 5.7 ml 12N aqueous HCl were added wile stirring. Stirring was maintained overnight at room temperature. The aqueous mixture was neutralized and extracted with methylene chloride. The organic phase was washed with brine, dried over MgSO4 and concentrated. The filtrate was concentrated and the residual oil was purified by chromatography on silica gel using ethyl acetate as eluent, affording 12 g of an oil pure by TLC.

後処理

  1. stirringStirring
  2. temperaturewas maintained overnight at room temperature
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. concentrationThe filtrate was concentrated
  8. customthe residual oil was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-d713bbc35f4146b29d03c1cbdb9d28f5
出典データセット
uspto-grants-1998_01
特許番号
US05712284

反応ノート

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