Hydrogen Bromide → HCID 57761092、化合物

HRID 230960ノート

反応式

HRID 230960 の反応式
[CH3:1][N:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6](N)=[CH:7][CH:8]=2)[CH2:3]1.N([O-])=O.[Na+].[BrH:19]>OS(O)(=O)=O.O>[Br:19][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH3:13])([CH3:12])[CH2:11][N:2]([CH3:1])[CH2:3]2)=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 260Hydrogen BromideHCID 18382547HCID 18382547、化合物HCID 23668193Sodium Nitrite

生成物 1

HCID 57761092HCID 57761092、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

To a cooled solution of 2,4,4-trimethyl-1,2,3,4-tetrahydro-isoquinolin-7-ylamine (prepared essentially as described in PCT International Application Publication Numbers WO 00/009,486, WO 00/007,993 or WO 98/41507; 330 mg, 1.734 mmol) in 75% aqueous H2SO4, add NaNO2 (132 mg, 1.91 mmol) in 1 ml of water, dropwise. Stir the solution at 0° C. for 30 minutes. Add CuBr (298 mg, 2.08 mmol) and 48% HBr (2 ml). Stir the mixture at 0° C. for 15 minutes. Heat the mixture at 60° C. for 30 minutes. Cool to room temperature, adjust the pH to 9-10, and extract with EtOAc. Wash with brine, dry the solution (Na2SO4), and concentrate under reduced pressure. Purify the residue by flash column chromatography eluting with EtOAc:Hexanes-(1:1) to afford 7-bromo-2,4,4-trimethyl-1,2,3,4-tetrahydro-isoquinoline.

後処理

  1. stirringStir the mixture at 0° C. for 15 minutes
  2. temperatureHeat the mixture at 60° C. for 30 minutes
  3. temperatureCool to room temperature
  4. extractionextract with EtOAc
  5. washWash with brine
  6. dry with materialdry the solution (Na2SO4)
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash column chromatography
  9. washeluting with EtOAc:Hexanes-(1:1)

出典と根拠

ORDレコード
ord-72ad198a92244789989e4b287d277b1b
出典データセット
uspto-grants-2009_07
特許番号
US07566712B2

反応ノート

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