Sodium hydride → 11-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-7,8,9,9a,10,11-hexahydro-5H-pyrido[3',2':4,5]pyrrolo[3,2-f]indolizine

HRID 535878ノート

反応式

HRID 535878 の反応式
[CH2:1]1[CH:5]2[CH2:6][C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][N:4]2[CH2:3][CH2:2]1)=[CH:13][CH:12]=[CH:11][N:10]=4.[H-].[Na+].[O:19]1[CH2:21][CH:20]1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>CN(C=O)C>[N:25]1[CH:26]=[CH:27][C:22]([CH:20]([OH:19])[CH2:21][N:8]2[C:7]3[CH2:6][CH:5]4[N:4]([CH2:3][CH2:2][CH2:1]4)[CH2:16][C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]2=3)=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 109534834-(Oxiran-2-yl)pyridineHCID 670365602,3,4,9,10,10a-hexahydro-1H-3a,8,9-triaza-cyclopenta[b]fluorene

生成物 1

HCID 5135667211-(2-(pyridin-4-yl)-2-(hydroxy)ethyl)-7,8,9,9a,10,11-hexahydro-5H-pyrido[3',2':4,5]pyrrolo[3,2-f]indolizine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triaza-cyclopenta[b]fluorene (1 g, 4.6 mmol) in DMF (20 mL) were portion wise added NaH (60%, 0.552 g, 13.8 mmol) and 4-(oxiran-2-yl)pyridine (0.709 g, 5.6 mmol). The reaction mixture was stirred at RT overnight. The progress of reaction mass was monitored by LCMS. The reaction mixture was quenched with ice cold water (300 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with water (10×100 mL) followed by brine (2×100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography followed by reverse phase HPLC to yield the title compound.

後処理

  1. customThe progress of reaction mass
  2. customThe reaction mixture was quenched with ice cold water (300 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layer was washed with water (10×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-87156b69d83d4ea9b5ac21f1e00f7de1
出典データセット
uspto-grants-2014_10
特許番号
US08859561B2

反応ノート

読み込み中…