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

HRID 727097노트

반응식

HRID 727097 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매2회

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d713bbc35f4146b29d03c1cbdb9d28f5
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712284

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