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

HRID 853768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853768
[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

Komponenten

6

Edukt 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 69471352HCID 69471352, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-54246b95d8a64c738c42af484b3d212f
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256186B2

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