Cornforth reagent → 1-[1-(3,4-Dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone

HRID 1250538ノート

反応式

HRID 1250538 の反応式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][CH:34]([OH:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]1

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 222576701(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropanol

生成物 1

HCID 222577801-[1-(3,4-Dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Pyridinium dichromate (4.0 g, 10.63 mmol) was added to a solution of 1(RS)-[1-(3,4-dichlorobenzyl)piperidin-4-ylmethyl]-2-methylpropanol (0.5 g, 1.5 mmol) in dimethylformamide (25 ml) at 0° C. The resulting solution was stirred at 0° C. until the starting material was consumed and then quenched with water, basified with 2N sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with water, brine, and dried over sodium sulfate. The residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes to give 1-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-3-methyl-2-butanone (0.32 g) as an oil.

後処理

  1. customwas consumed
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customThe residue was purified on silica gel with 25% acetone, 25% dichloromethane in hexanes

出典と根拠

ORDレコード
ord-445d9e1c5ba74a90aefc8b8a9ca08b3f
出典データセット
uspto-grants-2002_01
特許番号
US06339087B1

反応ノート

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