Potassium Carbonate → (S)-2-(3-(((3,4-Dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)methyl)(methyl)amino)propyl)isoindoline-1,3-dione

HRID 445907노트

반응식

HRID 445907 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH:14][CH3:15])[CH2:6]2.Br[CH2:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][N:14]([CH3:15])[CH2:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]1=[O:30])[CH2:6]2

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 11499437(S)-1-(3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)-N-methylmethanamine

생성물 1

HCID 68163162(S)-2-(3-(((3,4-Dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)methyl)(methyl)amino)propyl)isoindoline-1,3-dione수율 97%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

5.3 g (25.5 mmoles) of 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methyl-methanamine and 6.8 g (25.5 mmoles) of 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione are dissolved in 230 mL of acetone. 13 g (95 mmoles, 3.7 eq.) of potassium carbonate are added to the resulting solution. The mixture is then heated at reflux for 24 hours. After returning to ambient temperature, the potassium carbonate is filtered off and the filtrate is evaporated to dryness. The residue is taken up in water and extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and evaporated to dryness. 9.7 g of expected product are obtained in the form of a pale yellow oil.

후처리

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 24 hours
  3. customAfter returning to ambient temperature
  4. filtrationthe potassium carbonate is filtered off
  5. customthe filtrate is evaporated to dryness
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase is dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness

출처 및 근거

ORD 기록
ord-161b53f531d3469ba20d5b7b1a8fc47e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476426B2

반응 노트

불러오는 중…