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 445907ノート

反応式

HRID 445907 の反応式
[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

参加物

5

反応物 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

生成物 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-dione収率 97%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-161b53f531d3469ba20d5b7b1a8fc47e
出典データセット
uspto-grants-2013_07
特許番号
US08476426B2

反応ノート

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