Toluene → Methyl 12-cyclohexyl-3-(piperidin-3-yloxy)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate

HRID 1012287ノート

反応式

HRID 1012287 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:42]=[CH:41][C:18]3[C:19]4[N:23]([CH2:24][CH2:25][O:26][C:17]=3[CH:16]=2)[C:22]2[CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[CH:29]=[CH:30][C:21]=2[C:20]=4[CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH2:9]1)=O)(C)(C)C.C1(C)C=CC=CC=1>FC(F)(F)C(O)=O>[CH:35]1([C:20]2[C:21]3[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][C:22]=3[N:23]3[C:19]=2[C:18]2[CH:41]=[CH:42][C:15]([O:14][CH:10]4[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)=[CH:16][C:17]=2[O:26][CH2:25][CH2:24]3)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

参加物

4

反応物 2

HCID 1140TolueneHCID 23152338HCID 23152338、化合物

生成物 1

HCID 23152885Methyl 12-cyclohexyl-3-(piperidin-3-yloxy)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate収率 28.5%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

Methyl 3-(1-tert-butoxycarbonylpiperidin-3-yloxy)-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (0.68 g) was dissolved in trifluoroacetic acid (20 ml), and the mixture was stirred at room temperature for 3 hr. Toluene was added to the reaction mixture and the solvent was evaporated under reduced pressure. 4N HCl-ethyl acetate solution (2.0 ml) was added to the obtained residue and the mixture was stirred, and the solvent was evaporated under reduced pressure. The residue was neutralized with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:methanol=9:1) to give methyl 12-cyclohexyl-3-(piperidin-3-yloxy)-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (0.16 g, yield 17%).

後処理

  1. customthe solvent was evaporated under reduced pressure
  2. addition4N HCl-ethyl acetate solution (2.0 ml) was added to the obtained residue
  3. stirringthe mixture was stirred
  4. customthe solvent was evaporated under reduced pressure
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was successively washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. concentrationthe solvent was concentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (chloroform:methanol=9:1)

出典と根拠

ORDレコード
ord-b8abbe7220c541a8b27e8b5a2c2f8e20
出典データセット
uspto-grants-2011_07
特許番号
US07977331B1

反応ノート

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