Dicyclohexylcarbodiimide → (3aR,7aR)-7,7-diphenyl-2-[(S)-2-methoxy-2-phenylacetyl]-4-perhydroisoindolone

HRID 1029925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029925
O.OC1C2N=NNC=2C=CC=1.[CH3:12][O:13][C@@H:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15]([OH:17])=O.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[C:40]1([C:46]2([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[C@H:54]3[C@H:50]([CH2:51][NH:52][CH2:53]3)[C:49](=[O:55])[CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:56]1([C:46]2([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@H:54]3[C@H:50]([CH2:51][N:52]([C:15](=[O:17])[C@@H:14]([O:13][CH3:12])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:53]3)[C:49](=[O:55])[CH2:48][CH2:47]2)[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Komponenten

8

Edukt 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 643325(+)-Methoxyphenylacetic acidHCID 22843247(3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochlorideHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 22843244(3aR,7aR)-7,7-diphenyl-2-[(S)-2-methoxy-2-phenylacetyl]-4-perhydroisoindoloneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Hydroxybenzotriazole monohydrate (1 g) is added to a solution of (S)-α-methoxyphenylacetic acid (1.23 g) in dry dimethylformamide (20 cc), cooled to +5° C.; stirring is continued for 15 minutes and N,N'-dicyclohexylcarbodiimide (1.53 g) is then added. The mixture is stirred for 1 hour at +5° C. and a solution of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.43 g) and diisopropylethylamine (1.28 cc) in dry dimethylformamide (10 cc) is then added. The reaction mixture is stirred at +5° C. for 2 hours and then at ambient temperature for 2 hours. The reaction mixture, taken up in ethyl acetate (100 cc), is filtered; the filtrate is washed with distilled water (2×100 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (diameter 2.2 cm, height 27 cm), eluting with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 20 cc fractions. Fractions 68 to 177 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from isopropyl ether (15 cc); the crystals obtained are drained and then dried. (3aR,7aR)-7,7-diphenyl-2-[(S)-2-methoxy-2-phenylacetyl]-4-perhydroisoindolone (1.3 g) is obtained in the form of white crystals melting at 130° C.; [α]D20 =-230° (c=1, methanol).

Aufarbeitung

  1. temperaturecooled to +5° C.
  2. stirringThe mixture is stirred for 1 hour at +5° C.
  3. stirringThe reaction mixture is stirred at +5° C. for 2 hours
  4. waitat ambient temperature for 2 hours
  5. filtrationis filtered
  6. washthe filtrate is washed with distilled water (2×100 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  10. customThe residue is chromatographed on a silica gel column (diameter 2.2 cm, height 27 cm)
  11. washeluting with a mixture of cyclohexane and ethyl acetate (80/20 by volume)
  12. customcollecting 20 cc fractions
  13. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  14. customThe residue is crystallized from isopropyl ether (15 cc)
  15. customthe crystals obtained
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4efdaf62ebd443b5a7c8bfa101812426
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

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