methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate → methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927920ノート

反応式

HRID 927920 の反応式
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:18]C(=O)C(C)(C)C)[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]>S(=O)(=O)(O)O.CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:18])[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]

参加物

4

反応物 1

HCID 86713286methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate2 回

生成物 1

HCID 86713285methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate収率 77.4%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 887Methanol溶媒

実験手順

Concentrated sulfuric acid (5 drops) was added to a solution of methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate (Intermediate 30, 0.15 g) in methanol (5 mL) and the solution was stirred and heated at reflux for 48 hours. After cooling, the mixture was evaporated to low volume and the residue was dissolved in ethyl acetate and carefully washed with saturated aqueous sodium bicarbonate solution. The organic layer was filtered through a phase separator and the filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (0.09 g) as a brown gum.

後処理

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to low volume
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washcarefully washed with saturated aqueous sodium bicarbonate solution
  7. filtrationThe organic layer was filtered through a phase separator
  8. customthe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-f54dc18af68f404f882cf295af3eba88
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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