Hydrogen Bromide → HCID 57761092, 화합물

HRID 230960노트

반응식

HRID 230960 반응식
[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

참가 물질

6

반응물 3

HCID 260Hydrogen BromideHCID 18382547HCID 18382547, 화합물HCID 23668193Sodium Nitrite

생성물 1

HCID 57761092HCID 57761092, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-72ad198a92244789989e4b287d277b1b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566712B2

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