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Sodium Hydroxide → (4aS,10bR)-8-(4-methoxyphenoxy)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

HRID 521000
ノート
印刷プレビュー

反応式

HRID 521000 の反応式
[OH-].[Na+].FC(F)(F)C([N:7]1[C@@H:16]2[C@@H:11]([C:12]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[CH:17][C:13]=3[CH2:14][CH2:15]2)[CH2:10][CH2:9][CH2:8]1)=O>O1CCCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:12]3[C@@H:11]4[C@H:16]([CH2:15][CH2:14][C:13]=3[CH:17]=2)[NH:7][CH2:8][CH2:9][CH2:10]4)=[CH:27][CH:26]=1
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

4

反応物 2

HCID 14798Sodium HydroxideHCID 86654073cis-2,2,2-trifluoro-1-[8-(4-methoxy-phenoxy)-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl]-ethanone

生成物 1

HCID 86654075(4aS,10bR)-8-(4-methoxyphenoxy)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

1 M aqueous NaOH solution (10 mL) is added to a solution of cis-2,2,2-trifluoro-1-[8-(4-methoxy-phenoxy)-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl]ethanone (0.95 g) in tetrahydrofuran (10 mL) at room temperature. The resulting solution is stirred at 35° C. overnight and then cooled to room temperature. The solution is extracted with ethyl acetate, the combined extracts are washed with brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 95:5→70:30) to give the title compound as a colorless resin-like solid. Yield: 0.64 g (88% of theory); LC (method 1): tR=2.75 min; Mass spectrum (ESI+): m/z=310 [M+H]+.

後処理

  1. temperaturecooled to room temperature
  2. extractionThe solution is extracted with ethyl acetate
  3. washthe combined extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is evaporated
  6. customthe residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 95:5→70:30)

出典と根拠

ORDレコード
ord-ff22355466a24688b9a70b5a0c334e19
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09328072B2

反応ノート

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