Methyl iodide → HCID 67272383、化合物

HRID 251048ノート

反応式

HRID 251048 の反応式
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][NH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:18]I>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([CH3:18])[CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178453336HCID 178453336、化合物

生成物 1

HCID 67272383HCID 67272383、化合物収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

To a solution of [2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (512 mg, 2.42 mmol) in THF (20 mL) at −10° C. was added NaH (60%, 97 mg, 2.42 mmol). After stirring at −10° C. for 30 min, MeI (0.14 mL, 2.17 mmol) was added. After stirring at −10° C. for 2.5 h, the reaction mixture was concentrated to afford a yellow oil. Purification by flash column chromatography on silica gel using 2% MeOH/CH2Cl2 afforded [2-(1-methyl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester as a yellow oil (144 mg, 34%). Deprotection with TFA using General Procedure F gave [2-(1methyl-1H-imidazol-4-yl)-ethyl]-amine as a yellow oil (51 mg, 25%).

後処理

  1. stirringAfter stirring at −10° C. for 2.5 h
  2. concentrationthe reaction mixture was concentrated
  3. customto afford a yellow oil
  4. customPurification by flash column chromatography on silica gel using 2% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-697ca28db2024342a3be2a3ba364f81e
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

反応ノート

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