O-Cresol → 1-(tert-Butoxycarbonyl)-4-cyano-4-(2-methylphenoxymethyl)piperidine

HRID 890031ノート

反応式

HRID 890031 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21]([C:30]#[N:31])([CH2:24]OS(C)(=O)=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].O>CN(C)C=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21]([C:30]#[N:31])([CH2:24][O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 335O-CresolHCID 962WaterHCID 24758Sodium hydrideHCID 22248366HCID 22248366、化合物

生成物 1

HCID 222481081-(tert-Butoxycarbonyl)-4-cyano-4-(2-methylphenoxymethyl)piperidine収率 117.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

After dissolving 230 mg of 2-methylphenol in 20 ml of N,N-dimethylformamide, 43 mg of sodium hydride (70% suspension in oil) was added and the mixture was stirred at 80° C. for 30 minutes. Next, 224 mg of 1-(tert-butoxycarbonyl)-4-cyano-4-(methanesulfonyloxymethyl)piperidine was added and the mixture was stirred at 100° C. for 8 hours. After cooling it to room temperature, water was added and extraction was performed with ethyl acetate. The organic layer was washed with a 1N sodium hydroxide solution and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (273 mg, 100% yield).

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at 100° C. for 8 hours
  3. temperatureAfter cooling it to room temperature
  4. extractionextraction
  5. washThe organic layer was washed with a 1N sodium hydroxide solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-43624e9c3ae448cd83a26ae2f896fe3f
出典データセット
uspto-grants-2006_02
特許番号
US06995144B2

反応ノート

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