Triacetoxyperiodinane → Benzyl 4-formylpiperidine-1-carboxylate

HRID 220830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220830
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.C(Cl)(Cl)Cl.O>[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH:39]=[O:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

Produkt 1

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dess-Martin reagent (17 g, 39.6 mmol) was added portion-wise to a solution of 4-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester from Example E33.1 (8.33 g, 33 mmol) in dichloromethane (100 ml) at room temperature. The mixture was stirred for 3 h under an inert atmosphere then diluted with chloroform and water and the layers were partitioned. The organic layer was washed with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane) to yield the title compound (5.5 g, 66%).

Aufarbeitung

  1. customthe layers were partitioned
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ce0d9e545c534132b12a3dca31da0c12
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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