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Methanesulfonyl chloride → 1,2-Dihydro-1-[2-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068776
ノート
印刷プレビュー

反応式

HRID 1068776 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.S([O-])(=O)(=O)C.[NH:27]1[C:35]2[N:30]3[C:31](=[N:36][CH:37]=[C:29]3[C:28]1=[O:38])[CH:32]=[CH:33][CH:34]=2.C1CCN2C(=NCCC2)CC1>CCOCC.O.CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][N:27]2[C:35]3[N:30]4[C:31](=[N:36][CH:37]=[C:29]4[C:28]2=[O:38])[CH:32]=[CH:33][CH:34]=3)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 85257MethanesulfonateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 117449051,2-Dihydro-1,4,7b-triazacyclopent[cd]inden-2-one

生成物 1

HCID 21190114
1,2-Dihydro-1-[2-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one
収率 68.2%

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution prepared by dissolving 8.26 g (36.0 mM) of 2-(1-tert-butoxycarbonylpiperidin-4-yl)ethanol and 10.0 ml (72.0 mM) of triethylamine in 50 ml of ether was added 3.34 ml (43.2 mM) of methanesulfonyl chloride dropwise at 0° C. After completion of dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured in 100 ml of iced water and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate (MgSO4) and the solvent was distilled off under reduced pressure to recover the mesylate as solid. To a solution prepared by dissolving this mesylate and 10.37 g (36.0 mM) of 1,2-dihydro-1,4,7b-triazacyclopent[cd]inden-2-one.2NaCl in 25 ml of DMF was added 6.46 ml (43.2 mM) of DBU and the mixture was heated at 80° C. for 2 hours. After completion of the reaction, the reaction mixture was poured in iced water and the mixture was extracted with 200 ml of ethyl acetate. The organic layer was washed with 200 ml of purified water 3 times and further with 200 ml of saturated aqueous NaCl solution and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to provide 9.10 g (yield 68.2%) of the title compound as light-yellow solid.

後処理

  1. customTo a solution prepared
  2. additionAfter completion of dropwise addition
  3. customAfter completion of the reaction
  4. extractionthe mixture was extracted with 100 ml of ethyl acetate
  5. washThe organic layer was washed with 100 ml of saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto recover the mesylate as solid
  9. customTo a solution prepared
  10. temperaturethe mixture was heated at 80° C. for 2 hours
  11. customAfter completion of the reaction
  12. extractionthe mixture was extracted with 200 ml of ethyl acetate
  13. washThe organic layer was washed with 200 ml of purified water 3 times and further with 200 ml of saturated aqueous NaCl solution
  14. dry with materialdried over MgSO4
  15. distillationThe solvent was then distilled off under reduced pressure
  16. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

出典と根拠

ORDレコード
ord-138a95852baa46498655139717500bff
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06251905B1

反応ノート

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