Pyridine → 3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine

HRID 1774308ノート

反応式

HRID 1774308 の反応式
[CH3:1][CH:2]([CH2:4][CH:5]1[C:18](=O)[CH2:17][CH:16]2[N:7]([CH2:8][CH2:9][C:10]3[C:15]2=[CH:14][C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=3)[CH2:6]1)[CH3:3].Cl.NO.[N:27]1C=CC=CC=1>C(O)C>[CH2:4]([CH:5]1[CH2:6][N:7]2[CH2:8][CH2:9][C:10]3[C:15]([CH:16]2[CH2:17][CH:18]1[NH2:27])=[CH:14][C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=3)[CH:2]([CH3:3])[CH3:1]

参加物

5

反応物 3

HCID 1049PyridineHCID 6018TetrabenazineHCID 443297Hydroxyamine hydrochloride

生成物 1

HCID 120874003-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

HG-6 was also synthesized using the following alternative method: tetrabenazine (317 mg, 1 mmol) was dissolved in ethanol (EtOH, 10 ml) and hydroxylamine hydrochloride (70 mg, 1 mmol) was added, followed by the addition of pyridine (1 ml). The reaction was refluxed for 2 hours. After removing solvent, the residue was redissolved in methanol (MeOH, 10 ml). To this solution, MoO3 (80 mg) and sodium borohydride (80 mg) were slowly added. The reaction was stirred at room temperature for 24 hours and quenched with water. The aqueous solution was extracted with methylene chloride (10 ml) twice. The combined organic phase was washed with brine and dried with sodium sulfate. After removing solvent, the residue was purified by chromatography. Two hundred and fifty milligrams of HG-6 (3-isobutyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine) was obtained as white solid (yield: 78%).

後処理

  1. customHG-6 was also synthesized
  2. temperatureThe reaction was refluxed for 2 hours
  3. customAfter removing solvent
  4. dissolutionthe residue was redissolved in methanol (MeOH, 10 ml)
  5. additionTo this solution, MoO3 (80 mg) and sodium borohydride (80 mg) were slowly added
  6. customquenched with water
  7. extractionThe aqueous solution was extracted with methylene chloride (10 ml) twice
  8. washThe combined organic phase was washed with brine
  9. dry with materialdried with sodium sulfate
  10. customAfter removing solvent
  11. customthe residue was purified by chromatography

出典と根拠

ORDレコード
ord-f9b9c621464d4997805824616a9d5882
出典データセット
uspto-grants-2016_02
特許番号
US09260391B2

反応ノート

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