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Tetrahydrofuran → 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

HRID 1625166
ノート
印刷プレビュー

反応式

HRID 1625166 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[O:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[C@H:18]3[C:19](=[O:23])[N:20]([CH3:22])[CH2:21][C@@H:17]3[C:16]=2[CH:31]=1.[OH-:32].[Na+].[O:34]1CCCC1>>[CH3:22][N:20]1[CH2:21][CH:17]2[CH:18]([C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[O:26][C:15]3[CH:14]=[CH:13][C:12]([Cl:11])=[CH:31][C:16]=32)[CH2:19]1.[CH:18](/[C:19]([OH:23])=[O:34])=[CH:24]/[C:25]([OH:26])=[O:32]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 8028Tetrahydrofuran3 回HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 58729182(3aS,12bS)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

生成物 1

HCID 11954293
5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

反応条件

温度
2.5 °C

実験手順

Aluminum chloride (4.40 g) is added to tetrahydrofuran (100 mL) at 25-30° C. The solution is cooled to 0-5° C. and a solution of lithium aluminum hydride (1.80 g) in tetrahydrofuran (19 mL) is added. The mixture is stirred for 15-30 minutes. A solution of trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (10.0 g) in tetrahydrofuran (200 mL) is added by drops at 0-5° C. and the mixture is maintained for 1 hour. Sodium hydroxide solution (0.6N, 120 mL) is added at 0 to 5° C. The mixture is extracted with ethyl acetate (240 mL) and layers are separated, then the aqueous layer is washed with ethyl acetate (80 mL). The combined organic layer is washed with saturated brine solution (2×160 mL). The organic layer is dried over anhydrous sodium sulfate (10 g) and the solvent from the organic layer is evaporated at 45° C. The obtained residue is dissolved in 1-propanol (30 mL) at 25-30° C. This solution is added to a solution of maleic acid (5.3 g) in 1-propanol (20 mL) at 25-30° C. The mixture is stirred at 25-35° C. for 24 hours and the obtained solid is collected by filtration, washed with 1-propanol (5 mL), and dried under reduced pressure at 46° C., to afford 6.2 g of the title compound. PXRD pattern: complies with a reference pattern of monoclinic polymorph.

後処理

  1. temperaturethe mixture is maintained for 1 hour
  2. extractionThe mixture is extracted with ethyl acetate (240 mL) and layers
  3. customare separated
  4. washthe aqueous layer is washed with ethyl acetate (80 mL)
  5. washThe combined organic layer is washed with saturated brine solution (2×160 mL)
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate (10 g)
  7. customthe solvent from the organic layer is evaporated at 45° C
  8. dissolutionThe obtained residue is dissolved in 1-propanol (30 mL) at 25-30° C
  9. additionThis solution is added to a solution of maleic acid (5.3 g) in 1-propanol (20 mL) at 25-30° C
  10. stirringThe mixture is stirred at 25-35° C. for 24 hours
  11. filtrationthe obtained solid is collected by filtration
  12. washwashed with 1-propanol (5 mL)
  13. customdried under reduced pressure at 46° C.

出典と根拠

ORDレコード
ord-344d341d0d5d4a61b4dd6ebed69403b0
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08779161B2

反応ノート

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