Triacetoxyperiodinane → (3-Oxo-cyclohexyl)-carbamic acid tert-butyl ester

HRID 1749502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749502
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:11]([O:10][C:9](=[O:15])[NH:8][CH:4]1[CH2:5][CH2:6][CH2:7][C:2](=[O:1])[CH2:3]1)([CH3:14])([CH3:12])[CH3:13]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 21925254tert-Butyl (3-hydroxycyclohexyl)carbamate

Produkt 1

HCID 44228975(3-Oxo-cyclohexyl)-carbamic acid tert-butyl esterAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl (3-hydroxycyclohexyl)carbamate (4.40 g, 20.46 mmol) in DCM (250 mL) was added Dess-Martin periodinane (13.0 g, 30.70 mmol) in portions under cooling in an ice bath. The mixture was stirred at room temperature for 2 h. The reaction was diluted with DCM and washed with aqueous sodium carbonate. The separated organic layer was dried over anhydrous sodium sulfate and concentrated. The crude compound was purified by silica gel column chromatography (40% ethyl acetate in petroleum ether) to afford the title compound (4.0 g, 18.78 mmol, 91% yield). MS (ESI) m/z 214.1 [M+H]+.

Aufarbeitung

  1. temperatureunder cooling in an ice bath
  2. washwashed with aqueous sodium carbonate
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude compound was purified by silica gel column chromatography (40% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-0905cd3c69ee4e0fa96b06528047da41
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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