Benzyl (3-hydroxycyclohexyl)carbamate → Benzyl (3-oxocyclohexyl)carbamate

HRID 1013813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013813
[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14476840Benzyl (3-hydroxycyclohexyl)carbamateHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 10171453Benzyl (3-oxocyclohexyl)carbamateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Treat a solution of (3-hydroxy-cyclohexyl)-carbamic acid benzyl ester (15.5 g, 62.24) in dichloromethane (300 mL) with PCC (16.73 g, 77.81 mmol) and stir the mixture at room temperature for 12 hours. Filter the reaction mixture through celite. Remove the solvent in vacuo. Purify the residue on silica gel column using 25% to 50% ethyl acetate in hexanes gradient to afford 12.6 g (82%) of the title compound. MS (m/z): 248 (M+).

Aufarbeitung

  1. filtrationFilter the reaction mixture through celite
  2. customRemove the solvent in vacuo
  3. customPurify the residue on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-465aeaafce25464da4ee1600c86b5d31
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981918B2

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