Triacetoxyperiodinane → 1-(4-Chloro-benzenesulfonyl)-6-phenyl-piperidine-2-carbaldehyde

HRID 853768ノート

反応式

HRID 853768 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:23][OH:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[CH:23]=[O:24])(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 69471352HCID 69471352、化合物

生成物 1

HCID 184576701-(4-Chloro-benzenesulfonyl)-6-phenyl-piperidine-2-carbaldehyde収率 78%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of the 1-(4-chloro-benzenesulfonyl)-6-phenyl-piperidin-2-yl-methanol prepared according to Example 53 Preparation C Step 1 (300 mg; 0.82 mmol) in DCM (8 ml) was added Dess-Martin periodinane (850 mg; 2.0 mmol) followed by sodium bicarbonate (100 mg) and two drops of water. The mixture was stirred overnight at room temperature, then quenched with Et2O (20 mL), saturated NaHCO3 and sodium thiosulfite (2.0 g) for 20 minutes. The reaction was extracted with Et2O, dried over Na2SO4 and concentrated to provide 232 mg (78%) of 1-(4-chloro-benzenesulfonyl)-6-phenyl-piperidine-2-carbaldehyde as an oil.

後処理

  1. customquenched with Et2O (20 mL), saturated NaHCO3 and sodium thiosulfite (2.0 g) for 20 minutes
  2. extractionThe reaction was extracted with Et2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-54246b95d8a64c738c42af484b3d212f
出典データセット
uspto-grants-2007_08
特許番号
US07256186B2

反応ノート

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