Potassium Carbonate → (3aRS,7aRS)-2-benzyl-7,7-dimethyl-4-perhydroisoindolone

HRID 55406

Reaktionsgleichung

Reaktionsgleichung von HRID 55406
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1.C(O[CH2:15][N:16]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:17][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl.FC(F)(F)C(O)=O>[CH2:22]([N:16]1[CH2:17][CH:6]2[CH:7]([C:2]([CH3:9])([CH3:1])[CH2:3][CH2:4][C:5]2=[O:8])[CH2:15]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-HCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine

Produkt 1

HCID 67714335(3aRS,7aRS)-2-benzyl-7,7-dimethyl-4-perhydroisoindolone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5 g of 4,4-dimethylcyclohex-2-enone and 12.4 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 100 cm3 of dichloromethane are added, at a temperature of 10° C., 5 drops of trifluoroacetic acid. The reaction mixture is stirred at this temperature for 3 hours, then potassium carbonate is added and the solution is filtered through a sinter funnel and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 5.2 cm, height 25 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (85/15 by volume) and collecting 100 cm3 fractions. Fractions 39 to 63 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 3.64 g of (3aRS,7aRS)-2-benzyl-7,7-dimethyl-4-perhydroisoindolone are obtained in the form of a yellow oil.

Aufarbeitung

  1. filtrationthe solution is filtered through a sinter funnel
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 5.2 cm, height 25 cm)
  4. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (85/15 by volume)
  5. customcollecting 100 cm3 fractions
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-b19dfe6fd32d4b9786df94ca62e8fc2f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624950

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