Dimethyl Sulfoxide → 1-(2,2-Dimethylpropyl)piperidine-4-carbaldehyde

HRID 2192228ノート

反応式

HRID 2192228 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]1)[C:12]([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[CH2:11]([N:16]1[CH2:21][CH2:20][CH:19]([CH:22]=[O:23])[CH2:18][CH2:17]1)[C:12]([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 21060224[1-(2,2-Dimethylpropyl)piperidin-4-yl]methanol

生成物 1

HCID 593377161-(2,2-Dimethylpropyl)piperidine-4-carbaldehyde収率 85.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of oxalyl chloride (490 μL, 5.6 mmol) in DCM (10 mL) at −78° C. was added DMSO (796 μL, 11.2 mmol) dropwise followed by the addition of a solution of 20b (943 mg, 5.6 mmol) in DCM (2 mL). The mixture was stirred at −78° C. for 30 min and TEA (3.6 mL, 25.5 mmol) was added. The reaction was stirred at −78° C. for 5 min, warmed to rt and stirred at rt for 30 min. The reaction was quenched with water and extracted with DCM. The organic layers were combined and washed with water, dried over magnesium sulfate to give 20c as a yellow semi-solid (880 mg).

後処理

  1. stirringThe reaction was stirred at −78° C. for 5 min
  2. temperaturewarmed to rt
  3. stirringstirred at rt for 30 min
  4. customThe reaction was quenched with water
  5. extractionextracted with DCM
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate

出典と根拠

ORDレコード
ord-51a02bc53bdf496eb359031a3a46b719
出典データセット
uspto-grants-2012_12
特許番号
US08329718B2

反応ノート

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