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

HRID 853768노트

반응식

HRID 853768 반응식
[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

참가 물질

6

반응물 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 69471352HCID 69471352, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-54246b95d8a64c738c42af484b3d212f
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256186B2

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