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Methyl iodide → (S)-6-{3-(N-tert-butoxycarbonyl-N-methylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

HRID 1845954
ノート
印刷プレビュー

反応式

HRID 1845954 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[N:24][CH:23]=[CH:22]3)(=[O:18])=[O:17])[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:29]I>CN(C)C=O>[C:3]([O:7][C:8]([N:10]([C@H:11]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[N:24][CH:23]=[CH:22]3)(=[O:18])=[O:17])[CH2:12]1)[CH3:29])=[O:9])([CH3:6])([CH3:4])[CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66727094(S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

生成物 1

HCID 66726878(S)-6-{3-(N-tert-butoxycarbonyl-N-methylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

265 mg of sodium hydride was added with stirring under ice cooling to an N,N-dimethylformamide (10 mL) solution of 500 mg of (S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline obtained in Step 1. After stirring in this state for 30 minutes, 0.8 mL of methyl iodide was added dropwise to the reaction solution, and the mixture was further stirred for 30 minutes for reaction. The reaction was terminated by the dropwise addition of water in small portions under ice cooling to the reaction solution. Then, 50 mL of water was added thereto, followed by three extractions with 50 mL of ether. The combined organic layer was washed with 100 mL of saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (acetone:hexane=1:1) to obtain 100 mg of the compound of interest as a colorless oil (19%).

後処理

  1. stirringthe mixture was further stirred for 30 minutes for reaction
  2. customThe reaction was terminated by the dropwise addition of water in small portions under ice cooling to the reaction solution
  3. additionThen, 50 mL of water was added
  4. extractionfollowed by three extractions with 50 mL of ether
  5. washThe combined organic layer was washed with 100 mL of saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. customthe obtained crude product
  10. customwas purified by silica gel column chromatography (acetone:hexane=1:1)

出典と根拠

ORDレコード
ord-dd07e0266acf4c63b376d2c48109ad61
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08951997B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート